CN(OC)[C:3](=[O:17])[CH2:4][C:5]([C:8]1[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].CC(C[AlH]CC(C)C)C.S(=O)(=O)(O)O.C(OCC)(=O)C>C1COCC1>[O:15]1[C:16]2[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][CH:3]=[O:17])=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14]13-(2,3-Dihydrobenzofur-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide (950 mg) in THF (10 mL) was treated with DIBAL (1 M in toluene, 4.32 mL) at −78° C. After 45 minutes, the mixture was warmed to 0° C. for 5 minutes. 7 mL of aqueous sulfuric acid (1 M) and 20 mL of ethyl acetate were added. The organic phase was separated and the aqueous layer was extracted with 20 mL of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed to give 720 mg (98%) of 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanal as a yellow oil.
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