Tributylphosphine → HCID 69774117, compound

HRID 488448Notes

Reaction equation

[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:8][CH2:9][OH:10])=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:42]([O:44][C:45](=[O:58])[C@@H:46]([O:55][CH2:56][CH3:57])[CH2:47][C:48]1[CH:53]=[CH:52][C:51](O)=[CH:50][CH:49]=1)[CH3:43]>>[CH2:42]([O:44][C:45](=[O:58])[C@@H:46]([O:55][CH2:56][CH3:57])[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([O:10][CH2:9][CH:8]=[C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:6][CH:5]=2)[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:50][CH:49]=1)[CH3:43]

Participants

Reactant 3

HCID 13831Tributylphosphine

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

HCID 22270314HCID 22270314, compound

Product 1

HCID 69774117HCID 69774117, compoundYield 76.4%

Procedure

Reaction of 3,3-bis-biphenyl-4-yl-prop-2-en-1-ol (363 mg, 1.0 mmol), tributylphosphine (303 mg, 1.5 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (262 mg, 1.1 mmol) and azodicarboxylic dipiperidide (378 mg, 1.5 mmol) in an identical manner to example 3 gave the title compound (445 mg, 76%) containing 0.8 equivalents of ethyl acetate.

Sources & evidence

ORD record: ord-1ff47ef8bda94e69911d3854a826d0ab
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972294B1

Reaction notes

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