Triphenylphosphine → HCID 19027593, compound

HRID 864993Notes

Reaction equation

HRID 864993 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:13]O)[CH2:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>ClCCl>[C:1]([O:4][CH2:5][CH:6]([CH2:13][Br:34])[CH2:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 54465974HCID 54465974, compound

Product 1

HCID 19027593HCID 19027593, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-acetoxy-2-hydroxymethylbutyl acetate (11.04 g, 0.054 mol) and triphenylphospine (21.27 g, 0.081 mol) in dry dichloro methane (150 ml) was stirred at 0° C., and N-bromo-succinimide (14.43 g, 0.081 mol) was added in portions. The mixture was kept at 0° C. for 20 h, evaporated to small volume and stirred with 50 ml of ethyl acetate+n-hexane (1+1). The white triphenylphospine oxide was filtered off and washed with a little ethyl acetate+n-hexane (1-1). The combined filtrate was evaporated and purified on a 200 g SiO2 column with ethyl acetate+n-hexane (1+1) as eluent. The 250-550 ml fraction was evaporated in vacuum to give 11.90 g (82%) of pure 4-acetoxy-2-bromomethylbutyl acetate. TLC on silica (ethyl acetate+n-hexane 1+1): Rf 0.59.

Workup

  1. customevaporated to small volume
  2. filtrationThe white triphenylphospine oxide was filtered off
  3. washwashed with a little ethyl acetate+n-hexane (1-1)
  4. customThe combined filtrate was evaporated
  5. custompurified on a 200 g SiO2 column with ethyl acetate+n-hexane (1+1) as eluent
  6. customThe 250-550 ml fraction was evaporated in vacuum

Sources & evidence

ORD record
ord-1280e15616b043448e175535910f100f
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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