Hydrochloric Acid → 1-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol

HRID 396123Notes

Reaction equation

[C:1]([Mg]Br)([CH3:3])=[CH2:2].[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:21]=1)[CH:19]=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.Cl>C1COCC1>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[C:18]([CH:19]([OH:20])[C:1]([CH3:3])=[CH2:2])[CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

35.9 ml (16.33 mmol) of a 0.5 M isopropenylmagnesium bromide solution in THF are slowly added at −78° C. to a solution of 3.0 g (11.66 mmol) of 5-benzyloxy-2-nitrobenzaldehyde in 50 ml of THF. After addition is complete, the mixture is stirred at −78° C. for 2 h, then treated with 40 ml of water and warmed to room temperature. The mixture is treated with 10 ml of 1 N hydrochloric acid, the aqueous phase is extracted 2× with ethyl acetate, and the combined organic extracts are dried over sodium sulphate and freed from the solvent in vacuo. Purification of the crude product on silica gel (CH2Cl2) affords 1.7 g (48.7%) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol as a yellow oil.

Workup

additionAfter addition
temperaturewarmed to room temperature
extractionthe aqueous phase is extracted 2× with ethyl acetate
dry with materialthe combined organic extracts are dried over sodium sulphate
customPurification of the crude product on silica gel (CH2Cl2)

Sources & evidence

ORD record: ord-eb354f2a15d44414b896dc3d2e9aa075
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608049B2

Reaction notes

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