Triphenylphosphine → HCID 9870074, compound

HRID 1107570Notes

Reaction equation

HRID 1107570 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.O[CH:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[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:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]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

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 5462977Diethyl azodicarboxylateHCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Product 1

HCID 9870074HCID 9870074, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.17 g, 3.00 mmol) and 4-hydroxy-1-methylpiperidine (691 mg, 6.00 mmol) were dissolved in 50 mL of anhydrous tetrahydrofuran. This solution was stirred and triphenylphosphine (1.57 g, 6.00 mmol) and diethylazodicarboxylate (DEAD) (6.00 mmol) were added. The resulting solution was allowed to stir at room temperature for 18 hours. The solvent was removed under reduced pressure and the resulting mixture is flash chromatographed (eluent: 7:3 ethyl acetate:methanol) to give 834 mg of the title compound. Yield: 57%. MS(FD) 488(M+). EA calculated for C29H29NO4S: C, 71.43; H, 5.99; N, 2.87. Found: C, 71.14; H, 5.93; N, 2.61.

Workup

  1. stirringto stir at room temperature for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. customchromatographed (eluent: 7:3 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-ed78df2c489349f9aaac304babddc817
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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