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Methyl 4-Formylbenzoate → 4-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl ester

HRID 888
Notes
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Reaction equation

HRID 888 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[Br-].[O:14]1[CH2:19][CH2:18]C[O:16][CH:15]1[CH:20]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:21].[Li]CCCC>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:21][CH2:20][CH:15]2[O:14][CH2:19][CH2:18][O:16]2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 22107466[1-(1,3-Dioxan-2-yl)ethyl]triphenylphosphoniumbromideHCID 178418339Butyllithium

Product 1

HCID 867521644-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl esterYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The olefin was prepared from 4.3 g (26.2 mmol) of the aldehyde 167, 13.94 g of [1-(1,3-dioxan-2-yl)ethyl]triphenylphosphoniumbromide and 12.6 mL (32.0 mmol) of n-BuLi in 75 mL of THF as described for the synthesis of 156 in Example 8. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.27 g of the olefin 168. 1H NMR consistent with the product.

Workup

  1. washFlash chromatography (elution with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6120ae4e516c4335a3f2eb3671f18da1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723459

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes