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

HRID 1662562
Notes
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Reaction equation

HRID 1662562 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 113463223-Tert-butyldimethylsilyloxy-2,5-difluorobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 577069101-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-olYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred for 30 minutes at ambient temperature
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. additiondiluted with EtOAc
  5. washThe organic layers were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes