Diisopropylamine → alpha-(4-Benzyloxyphenyl)-alpha-hydroxy-N,N-dimethyl-thioacetamide

HRID 650020Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:29][N:30]([CH3:33])[CH:31]=[S:32]>C1COCC1>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH:25]([OH:26])[C:31]([N:30]([CH3:33])[CH3:29])=[S:32])=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of distilled diisopropylamine (22.9 mL, 175 mmol) in 400 mL of anhydrous THF at −78° C. was added 1.6 M n-butyllithium in hexanes (100 mL, 160 mmol) over a period of 45 min. The mixture was stirred at −78° C. for 1.5 h. To the solution was cannulated over a period of 1 h a solution of 4-benzyloxybenzaldehyde (30.9 g, 146 mmol) and N,N-dimethylthioformamide (13.7 mL, 160 mmol) in 100 mL of distilled THF. The reaction mixture was stirred at −78° C. for 16 h. The reaction was then quenched with 500 mL of saturated NH4Cl solution. The mixture was extracted with EtOAc (3×1 L), and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was then recrystallyzed from EtOAc/hexanes to afford 20.0 g (66.5 mmol, 46%) of an off-white solid.

Workup

waitTo the solution was cannulated over a period of 1 h
stirringThe reaction mixture was stirred at −78° C. for 16 h
customThe reaction was then quenched with 500 mL of saturated NH4Cl solution
extractionThe mixture was extracted with EtOAc (3×1 L)
dry with materialthe combined organic layers were dried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-652d0d4055cd475da59033d9071b4c54
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271227B1

Reaction notes

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