Water → HCID 20355562, compound

HRID 598529Notes

Reaction equation

HRID 598529 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]([Mg]Br)=[CH2:13].[C:16](OC(=O)C)(=[O:18])[CH3:17].O>C1COCC1.CCOC(C)=O>[C:16]([O:11][CH:10]([CH:12]=[CH2:13])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 108989(Phenylmethoxy)acetaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 20355562HCID 20355562, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

Benzyloxyacetaldehyde 1 (220 g, 1.46 mol) in anhydrous THF (140 mL) was added drop wise to a stirred 1 M solution of vinyl magnesium bromide in THF (1.89 L) previously cooled to −5° C. When the addition was complete, the mixture was allowed to stir at −5° C. for an additional 30 minutes after which time TLC analysis showed a complete reaction. Acetic anhydride (222 mL, 240 g, 2.35 mol, 1.6 eq) was then added and the mixture allowed to slowly warm-up to room temperature overnight. Iced water (1 L) was then added to the reaction followed by EtOAc (700 mL) and the mixture stirred for 10 min. The layers were separated and the aqueous layer extracted with EtOAc (700 mL). The combined organics were washed with brine (700 mL), dried (MgSO4) and concentrated in vacuo to give the crude product as an orange oil. Purification through a silica pad afforded the acetate 2 as a yellow oil (309 g, 97%).

Workup

  1. additionWhen the addition
  2. customa complete reaction
  3. temperatureto slowly warm-up to room temperature overnight
  4. stirringthe mixture stirred for 10 min
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with EtOAc (700 mL)
  7. washThe combined organics were washed with brine (700 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give the crude product as an orange oil
  11. customPurification through a silica pad

Sources & evidence

ORD record
ord-222b20bb94184734becab872065c7527
Source dataset
uspto-grants-2011_03
Patent number
US07897629B2

Reaction notes

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