Dimethylformamide → HCID 11447610, compound

HRID 53239Notes

Reaction equation

C([Li])(C)(C)C.Br[C:7]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=1.CN(C)[CH:24]=[O:25]>C1COCC1>[C:18]([C:16]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([CH:24]=[O:25])[CH:17]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: -78 °C

Procedure

t-Butyllithium (11.9 mL, 20.3 mmol, 1.7M in pentane) is added dropwise to a solution of 5-bromo-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan (3.60 g, 12.7 mmol) in 50 mL of anhydrous THF at -78° C.; the resulting reaction mixture is stirred at -78° C. for 15 min and N,N-dimethylformamide (1.0 mL, 13.0 mmol) is introduced. The reaction mixture is kept at -78° C. for 0.5 h, quenched with water, warmed to room temperature, and extracted with ether. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (10%→20% ether-hexane) gives 0.83 g (28%) of 7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-formylbenzo[b]furan as a yellowish oil.

Workup

customthe resulting reaction mixture
waitThe reaction mixture is kept at -78° C. for 0.5 h
customquenched with water
temperaturewarmed to room temperature
extractionextracted with ether
washThe extract is washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by flash column chromatography on silica gel (10%→20% ether-hexane)

Sources & evidence

ORD record: ord-8382aa719f13415ba067e4a9a410d282
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618835

Reaction notes

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