Benzyl Alcohol → 3-[2-(4-Benzyloxycarbonylphenyl)ethyl]-4-hydroxybenzofuran

HRID 230921Notes

Reaction equation

HRID 230921 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[C:16]3[C:17]([OH:21])=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH:13]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:22](O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:22]([O:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[C:16]3[C:17]([OH:21])=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH:13]=2)=[CH:8][CH:9]=1)=[O:3])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67136040HCID 67136040, compound

Product 1

HCID 671358883-[2-(4-Benzyloxycarbonylphenyl)ethyl]-4-hydroxybenzofuranYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[2-(4-carboxyphenyl)ethyl]-4-hydroxybenzofuran (0.25 g) in tetrahydrofuran (1 mL) were added benzyl alcohol (96 mg), triphenylphosphine (0.26 g) and diethyl azodicarboxylate (40% toluene solution, 0.43 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1) to give the title compound (0.26 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-e2ceb86c5cc54ee2bfcb9681ed3591bb
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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