Toluene → HCID 86646155, compound

Reaction equation

[CH2:1]([CH:4]1[CH2:8][CH2:7][O:6][CH:5]1[OH:9])[CH:2]=[CH2:3].[CH2:10]([O:12]C(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[C:34]1([CH3:40])C=CC=C[CH:35]=1>>[OH:12][CH2:10][CH2:3][CH:2]([CH2:40][CH:34]=[CH2:35])/[CH:1]=[CH:4]/[C:5]([O:6][CH2:7][CH3:8])=[O:9]

Participants

Reactant 3

HCID 1140Toluene

HCID 135457673-(Prop-2-en-1-yl)oxolan-2-ol

HCID 178473672HCID 178473672, compound

Product 1

HCID 86646155HCID 86646155, compound

Procedure

3-allyl-tetrahydrofuran-2-ol (18 g, 140 mmol) and ethoxycarbonyl triphenylphosphorane (35 g, 104 mmol) were stirred overnight in toluene (200 mL). The reaction solution was concentrated, and the residue was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (15.8 g, 61.1%).

Workup

concentrationThe reaction solution was concentrated
customthe residue was purified by silica gel column chromatography
customto obtain the compound of interest as an oil substance (15.8 g, 61.1%)

Sources & evidence

ORD record: ord-27af5f9a4e42434abf0c6c363f642844
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947738B2

Reaction notes

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