CBr4 triphenylphosphine → (+) Methyl 6(R)-hydroxy-7-eicosynoate

HRID 478016Notes

Reaction equation

[OH:1][CH:2]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[OH:1][C@@H:2]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

Reactant 2

HCID 11387777CBr4 triphenylphosphine

HCID 15003196Methyl 6-(+/-)-hydroxy-7-eicosynoate

Product 1

HCID 15003197(+) Methyl 6(R)-hydroxy-7-eicosynoate

Procedure

This compound was prepared by reaction of methyl 6-(±)-hydroxy-7-eicosynoate (preparative example V) with CBr4 /Ph3P reagent in exactly the same manner as described in preparative example VIII. Note: By use of the corresponding 6-R, and 6-S alcohols (preparative example VI) the optically active (+) and (-) 6-bromo-7-eicosynoates were also obtained.

Sources & evidence

ORD record: ord-3903ff80f62548ec8f466d5a6c2990b7
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889873

Reaction notes

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