CBr4 triphenylphosphine → HCID 131715269, compound

HRID 2309751Notes

Reaction equation

[OH:1][CH:2]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:22][C:23]([O-:25])=[O:24].C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[OH:1][C@@H:2]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:22][C:23]([O-:25])=[O:24]

Participants

Reactant 2

HCID 11387777CBr4 triphenylphosphine

HCID 131715270HCID 131715270, compound

Product 1

HCID 131715269HCID 131715269, compound

Procedure

This compound was prepared by reaction of 6(±)-hydroxy-7-eicosyn-methylcarboxylate (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-yne-eicosanoates were also obtained.

Sources & evidence

ORD record: ord-639dcdc6dd4e4de7bab59420c28405e1
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04696946

Reaction notes

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