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Triphenylphosphine → 6-Methoxy-2-(4-Methoxyphenyl)-3-(4-[2-Pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene

HRID 1107579
Notes
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Reaction equation

HRID 1107579 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:19])[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1.[N:29]1([C@@H:34]2[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]2O)[CH2:33][CH2:32][CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:19])[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH:34]4[N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiopheneHCID 10103566rel-(1R,2R)-2-(1-Pyrrolidinyl)cyclohexanol

Product 1

HCID 99589906-Methoxy-2-(4-Methoxyphenyl)-3-(4-[2-Pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene
Yield 35%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.27 g, 3.25 mmol), trans-2-pyrrolidinylcyclohexanol (1.10 g, 6.50 mmol), triphenylphosphine (1.70 g, 6.50 mmol), and DEAD (6.50 mmol) were converted to product by the procedure of Example 11 to give 615 mg of the title compound. Yield: 35%. MS(FD) 541(M+). IR (CHCl3) ν max 3009, 2940, 1645, 1597, 1476, 1254, 1166.

Sources & evidence

ORD record
ord-f804d86175fc43019aafcc809870b97c
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06060488

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes