Ethyl Acetate → HCID 58816128, compound

HRID 2219219Notes

Reaction equation

HRID 2219219 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1.[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24]Br)[CH3:21].C(OCC)(=O)C>CN(C=O)C.O>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:17][CH2:24][CH:23]([O:26][CH2:27][CH3:28])[O:22][CH2:20][CH3:21])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 701194-Bromobenzyl alcoholHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58816128HCID 58816128, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium bis(trimethylsilyl)amide (12.1 mL, 1 N in THF) is added to a stirred solution of 4-bromo-benzylalcohol (2.05 g, 11.0 mmol) in dry DMF (7 mL) at ambient temperature. The mixture is stirred for 5 min before it is treated with bromoacetaldehyde diethyl acetal (1.99 mL, 13.2 mmol). The resultant mixture is allowed to stir at ambient temperature for 20 hours. Ethyl acetate (60 mL) and water (60 mL) are added to the mixture. The organic layer is separated, washed with half-saturated brine, dried, filtered and concentrated. After MPLC separation on silica (gradient 0-8% ethyl acetate in hexane), 1.86 g (56% yield) title compound is obtained as colorless oil.

Workup

  1. stirringto stir at ambient temperature for 20 hours
  2. customThe organic layer is separated
  3. washwashed with half-saturated brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter MPLC separation on silica (gradient 0-8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1922388f7efc4bb48d2dbcbf25a9cdef
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

Loading…