Triphenylphosphine → HCID 67058255, compound

HRID 1515106Notes

Reaction equation

[CH2:1]([O:3][C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH3:2].[CH3:17][C:18]1([CH3:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20](O)[CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:17][C:18]1([CH3:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]([O:16][C:13]2[CH:14]=[CH:15][C:10]([C@@H:4]([O:3][CH2:1][CH3:2])[CH2:5][C:6]([O:8][CH3:9])=[O:7])=[CH:11][CH:12]=2)[CH2:19]1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl (3S)-3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.446 mmol) produced in Example 41 (41C) and 3,3-dimethylindan-1-ol (110 mg, 0.669 mmol) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40% diethyl azodicarboxylate toluene solution (309 μL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (101 mg, yield: 62%).

Workup

temperatureAfter the reaction solution was cooled to room temperature
distillationthe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound
customwas obtained as a yellow oily substance (101 mg, yield: 62%)

Sources & evidence

ORD record: ord-1e17dc562f1f404bba0b95d6656d0821
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222281B2

Reaction notes

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