Triphenylphosphine → 5-((4-Phenyl-5-trifluoromethyl-2-thienyl)methoxy)-1-indanone

HRID 1352197Notes

Reaction equation

HRID 1352197 reaction equation
[OH:1][CH2:2][C:3]1[S:4][C:5]([C:14]([F:17])([F:16])[F:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.O[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[CH2:23][CH2:22]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:8]1([C:6]2[CH:7]=[C:3]([CH2:2][O:1][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[CH2:23][CH2:22]4)[S:4][C:5]=2[C:14]([F:17])([F:15])[F:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2331475-Hydroxy-1-indanoneHCID 2781490(4-Phenyl-5-(trifluoromethyl)thiophen-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 211000345-((4-Phenyl-5-trifluoromethyl-2-thienyl)methoxy)-1-indanoneYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.25 g (0.97 mmol) of 2-hydroxymethyl-4-phenyl-5-trifluoromethyl-thiophene (from Step D), 0.17 g (1.16 mmol) of 5-hydroxy-1-indanone and 0.31 g (0.16 mmol) of triphenylphosphine in 2.5 mL of THF at 0° C. was treated with 0.18 mL (0.16 mmol) of diethylazodicarboxylate. The resulting mixture was warmed to rt, and stirred for 2 h. The reaction was loaded onto silica gel and eluted with 33% ethyl acetate/hexanes to give 0.35 g (0.90 mmol, 78%) of the title compound as a white solid: 1H NMR (500 MHz) δ 7.76 (d, J=8.3 Hz, 1H), 7.42–7.47 (m, 5H), 7.14 (s, 1H), 7.01–7.03 (m, 2H), 5.34 (s, 2H), 3.15 (t, J=5.9 Hz, 2H), 2.72 (t, J=6.0 Hz, 2H); ESI-MS 388.9 (M+H).

Workup

  1. washeluted with 33% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-dde94149a79344be89764af67189b398
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Reaction notes

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