Triphenylphosphine → HCID 56611422, compound

HRID 1638571Notes

Reaction equation

HRID 1638571 reaction equation
[OH:1][C@H:2]([C@@H:11](O)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][C@@H:4]([CH:8]([CH3:10])[CH3:9])[C:5]([OH:7])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>C1C=CC=CC=1.CCOCC>[Br:36][C@H:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C@@H:2]([OH:1])[CH2:3][C@@H:4]([CH:8]([CH3:10])[CH3:9])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 56630262HCID 56630262, compound

Product 1

HCID 56611422HCID 56611422, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of the γ-lactone of (2S,4S,5S)-4,5-dihydroxy-2-isopropyl-7-methyloctanoic acid from Preparation IIIA (0.214 g., 1 mmol) and triphenylphosphine (0.289 g., 1.1 mmol) in benzene (3 ml) is cooled in an ice bath and treated during 5-10 minutes with N-bromosuccinimide (0.196 g., 1.1 mmol). The mixture is kept cold for an additional 30 minutes and then at ambient temperature for 4 hours. It is diluted with Et2O and filtered. The filtrate is con-centrated and the residue chromatographed on silica gel (100 g.) with 7.5% EtOAc-hexane. The product, the γ-lactone of (2S,4S,5R)-5-bromo-4-hydroxy-2-isopropyl-7-methyloctanoic acid, thus obtained was crystallized from cold pentane to give 0.061 g., m.p. 62.5°-63.5° C. and 0.054 g., m.p. 60°-62.5° C.

Workup

  1. temperatureis cooled in an ice bath
  2. waitat ambient temperature for 4 hours
  3. filtrationfiltered
  4. customthe residue chromatographed on silica gel (100 g.) with 7.5% EtOAc-hexane

Sources & evidence

ORD record
ord-5af084ea27434330b43d07866a44cfd0
Source dataset
uspto-grants-1989_11
Patent number
US04880781

Reaction notes

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