2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 86696655, compound

HRID 1774153Notes

Reaction equation

HRID 1774153 reaction equation
[Si:1]([O:8][CH2:9][CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][C:14]=1[F:21]>C1COCC1>[Si:1]([O:8][CH2:9][CH:10]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([F:21])[CH:15]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 178505943HCID 178505943, compound

Product 1

HCID 86696655HCID 86696655, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(tert-butyldimethylsilyloxy)acetaldehyde (2.00 g, 10.3 mmol) in dry THF (40 mL) was placed in an ice bath, and (4-chloro-3-fluorophenyl)magnesium bromide (24.8 mL, 12.4 mmol) was added dropwise via a syringe. The reaction mixture was stirred at 0° C. for 1 hour and then carefully quenched by dropwise addition of water. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and saturated aqueous NH4Cl. The organics were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/EtOAc (20:1) to give 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanol (2.92 g, 9.58 mmol, 92.8% yield) as an oil.

Workup

  1. customcarefully quenched by dropwise addition of water
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc and saturated aqueous NH4Cl
  4. customThe organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluting with hexanes/EtOAc (20:1)

Sources & evidence

ORD record
ord-65622ea304ee479ab2103d2977e6b1ba
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

Loading…