Dimethyl Sulfoxide → 1-(Diphenylmethyl)azetidin-3-one

HRID 2307216Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([CH:17]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl.O>[C:23]1([CH:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:18]2[CH2:21][C:20](=[O:22])[CH2:19]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: -50 °C

Procedure

Dimethyl sulfoxide (0.36 mL, 5 mmol) was added dropwise to a stirred solution of oxalyl chloride (0.40 mL, 4.6 mmol) in dichloromethane (20 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes then a solution of 1-(diphenylmethyl)-3-azetidinol (1.0 g, 4.2 mmol) in dichloromethane (20 mL) was added dropwise. The mixture was warmed to −50° C. and sired for 30 minutes. Triethylamine (2.9 mL, 21 mmol) was added and the mixture warmed to room temperature. After 1 hour, water (50 mL) was added and the mixture extracted with dichloromethane (4×50 mL). The combined organic extracts were washed (brine), dried (Na2SO4) and concentrated in vacuo to give 1-diphenylmethyl-3-azetidinone (3) as a pale yellow crystalline solid (1.0 g, 99%) (lit. (S. S. Chattetjee and A. Shoeb, Synthesis, 1973,153) m.p. 82° C.).

Workup

waitsired for 30 minutes
temperaturethe mixture warmed to room temperature
waitAfter 1 hour
extractionthe mixture extracted with dichloromethane (4×50 mL)
washThe combined organic extracts were washed (brine)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dcd4bf7d4dc249f78469725ddb663d1a
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831078B1

Reaction notes

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