Water → Tert-butyl 3-(4-formylphenyl)-2,2-dimethylpropionate

HRID 353165Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=1.CN(C)[CH:26]=[O:27].O>CCCCC.O1CCCC1>[CH:26]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=1)=[O:27]

Participants

Conditions

Temperature: -20 °C

Procedure

At −75° C., 13.5 ml (22.98 mmol) of a 1.7 M tert-butyllithium solution in pentane are slowly added to a solution of 6.00 g (19.16 mmol) of tert-butyl 3-(4-bromophenyl)-2,2-dimethylpropionate (Example I-2) in 80 ml of tetrahydrofuran, the temperature being kept below −60° C. The mixture is stirred for 15 min, and 1.82 g (24.90 mmol) of N,N-dimethylformamide are then added and the mixture is stirred at −75° C. for a further 4 h. The mixture is slowly warmed to −20° C. and, with vigorous stirring, admixed with 20 ml of water, and then warmed to room temperature. The aqueous phase is extracted 3× with diethyl ether and the combined organic phases are dried over sodium sulfphate/sodium carbonate and freed from the solvent under reduced pressure. Distillation of the residue under oilpump vacuum gives 2.54 g (51%) of tert-butyl 3-(4-formylphenyl)-2,2-dimethylpropionate.

Workup

customAt −75° C.
custombeing kept below −60° C
stirringthe mixture is stirred at −75° C. for a further 4 h
temperaturewarmed to room temperature
extractionThe aqueous phase is extracted 3× with diethyl ether
dry with materialthe combined organic phases are dried over sodium sulfphate/sodium carbonate
distillationDistillation of the residue under oilpump vacuum

Sources & evidence

ORD record: ord-4b7e96fa0b7d44c1a242c01668ae5bd7
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750236B2

Reaction notes

Loading…