1: 95 percent / LiAlH4 / diethyl ether 2: 1) DMSO, oxalyl chloride 2) Et3N / 1) CH2Cl2, -60 deg C, 2 min; 2) -60 to 20 deg C, 2 h 3: 1) n-BuLi / 1) THF, hexane, -60 to -10 deg C 2) THF, hexane, 20 deg C, 1 h View Scheme

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1: 1) DMSO, oxalyl chloride 2) Et3N / 1) CH2Cl2, -60 deg C, 2 min; 2) -60 to 20 deg C, 2 h 2: 1) n-BuLi / 1) THF, hexane, -60 to -10 deg C 2) THF, hexane, 20 deg C, 1 h View Scheme

n-butyllithium 1) THF, hexane, -60 to -10 deg C 2) THF, hexane, 20 deg C, 1 h; Yield given. Multistep reaction;