Triphenylphosphine → HCID 86699450, compound

HRID 573518Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:36]([O:54][CH2:55][C@H:56](O)[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49][CH2:50][CH2:51][CH2:52][CH3:53].C1(P([N:81]=[N+:82]=[N-:83])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH2:36]([O:54][CH2:55][C@@H:56]([N:81]=[N+:82]=[N-:83])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

Conditions

Temperature: 0 °C

Procedure

Triphenyl phosphine (14.4 g, 55 mmol) was dissolved in THF and cooled to 0° C. under nitrogen. Di-tertbutyl azodicarboxylate (13.7 g, 59.5 mmol) was added slowly and the reaction was stirred for 30 mins. Then the alcohol (20 g, 45.8 mmol) was added dropwise and allowed to stir for 10 mins, then diphenyl phosphorylazide (15.1 g, 55 mmol) was added and allowed to stir overnight, warming to ambient temperature. The reaction was evaporated to dryness in vacuo and directly loaded onto a silica gel column and eluted with 0-10% ethyl acetate/hexane gradient to provide (2S)-2-azidoundecyl(9Z,12Z)-octadeca-9,12-dien-1-yl ether which was carried directly into the next reaction without characterization.

Workup

stirringto stir for 10 mins
stirringto stir overnight
temperaturewarming to ambient temperature
customThe reaction was evaporated to dryness in vacuo
washeluted with 0-10% ethyl acetate/hexane gradient

Sources & evidence

ORD record: ord-499c31acb1984c408acbe4e6f4e0bedd
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029604B2

Reaction notes

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