Triphenylphosphine → HCID 69774062, compound

HRID 488446Notes

Reaction equation

HRID 488446 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4](/[C:7](/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8]\[CH2:9][OH:10])=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[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].N(C(OCC)=O)=NC(OCC)=O>>[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:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:5]=2)/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:50][CH:49]=1)[CH3:43]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 69774094HCID 69774094, compound

Product 1

HCID 69774062HCID 69774062, compoundYield 53%

Procedure

Reaction of (Z)-3-biphenyl-4-yl-3-phenyl-prop-2-en-1-ol (171 mg, 0.60 mmol), triphenylphosphine (142 mg, 0.63 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (149 mg, 0.63 mmol) and diethyl azodicarboxylate (95 mg, 0.55 mmol) in an identical manner to example 1 gave the title compound (160 mg, 53%).

Sources & evidence

ORD record
ord-c57ccb09f5024fe5bb20609f9bae19be
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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