Ethyl Acetate → HCID 22678860, compound

HRID 1387492Notes

Reaction equation

HRID 1387492 reaction equation
[CH2:1]([C:5](O)([CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[Br-].[Br:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([C:5]([Br:19])([CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 10137025HCID 10137025, compoundHCID 15695649HCID 15695649, compound

Product 1

HCID 22678860HCID 22678860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.1 g (25 mmol) of benzyl alcohol obtained from Step 2 in 100 mL of DMF at −40 C. was added 47 g (50 mmol) of bromotriphenyphosphonium bromide (Aldrich). The resulting solution was stirred cold for 30 min, then was allowed to warm to 0 C. To the mixture was added 10% solution of sodium sulfite and ethyl acetate. The extract was washed a few times with water, dried (MgSO4), and concentrated in vacuo. The mixture was stirred in small amount of ethyl acetate/hexane mixture (1:4 ratio) and filtered through a pad of silica gel, eluting with same solvent mixture.

Workup

  1. temperatureto warm to 0 C
  2. washThe extract was washed a few times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. stirringThe mixture was stirred in small amount of ethyl acetate/hexane mixture (1:4 ratio)
  6. filtrationfiltered through a pad of silica gel
  7. washeluting with same solvent mixture

Sources & evidence

ORD record
ord-0583fba457e34adba9cf81fd690f8963
Source dataset
uspto-grants-2001_07
Patent number
US06268392B1

Reaction notes

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