3-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehyde → 1-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-ol

HRID 1662562Notes

Reaction equation

[Si:1]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:14]=[C:15]([F:17])[CH:16]=1)[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:19]([Mg]Br)[CH3:20]>C1COCC1>[Si:1]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:12]([OH:13])[CH2:19][CH3:20])[CH:14]=[C:15]([F:17])[CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A 200 mL round bottom flask was charged with 90.B (1.38 g, 5.1 mmol) and THF (10 mL) and cooled to −78° C. under N2. To the cold solution was added ethylmagnesium bromide (3.0 M in ether) (commercially available from Aldrich) (5.1 mL, 15 mmol) dropwise. The mixture was stirred for 30 minutes at −78° C. The cooling bath was removed, and the mixture was stirred for 30 minutes at ambient temperature. The reaction was quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The organic layers were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-15% EtOAc/hexane) to afford 90.C (0.48 g, 31% yield) as a colorless oil.

Workup

customThe cooling bath was removed
stirringthe mixture was stirred for 30 minutes at ambient temperature
customThe reaction was quenched with saturated aqueous ammonium chloride
additiondiluted with EtOAc
washThe organic layers were washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-15% EtOAc/hexane)

Sources & evidence

ORD record: ord-4a1a0ba155094d9a9ec05b5d3cc96d8e
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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