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

HRID 1107575Notes

Reaction equation

HRID 1107575 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.[CH2:29]([N:36]1[CH2:40][CH2:39][CH:38](O)[CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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:38]4[CH2:39][CH2:40][N:36]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:37]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

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 69889N-benzyl-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylateHCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Product 1

HCID 99155176-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiopheneYield 95.3%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.17 g, 3.00 mmol), 1-benzyl-3-hydroxypyrrolidine (1.06 g, 6.00 mmol), triphenyiphosphine (1.57 g, 6.00 mmol), and DEAD (6.0 mmol) were converted to product by the procedure of Example 1 to g ive 1.57 g of the title compound. Yield: 95.3%. MS(FD) 549(M+). IR (CHCl3) ν max 3033, 3010, 2971, 2842, 1646, 1599, 1476, 1254, 1167.

Sources & evidence

ORD record
ord-6b2c74fd54614a80b2dd180fa4ebcc07
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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