4-Allyl-3,5-dihydroxy-benzoic acid methyl ester → 4-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1177082Notes

Reaction equation

HRID 1177082 reaction equation
COC(C1C=C(OC)C=C2OC(C)CC=12)=O.[CH3:17][O:18][C:19](=[O:31])[C:20]1[CH:25]=[C:24]([OH:26])[C:23]([CH2:27][CH:28]=[CH2:29])=[C:22]([OH:30])[CH:21]=1>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH3:17][O:18][C:19]([C:20]1[CH:25]=[C:24]([OH:26])[C:23]2[CH2:27][CH:28]([CH3:29])[O:30][C:22]=2[CH:21]=1)=[O:31]

Participants

4

Reactant 2

HCID 537917924-Allyl-3,5-dihydroxy-benzoic acid methyl esterHCID 543897576-Methoxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 595600564-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-Catalyst

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1d, from zirconium(IV) chloride and 4-allyl-3,5-dihydroxy-benzoic acid methyl ester (10b) (85 mg, 0.41 mmol). Purification by flash column chromatography eluting with 15-25% EtOAc in hexane gave a pale yellow solid (58 mg, 68% yield). 1H NMR (400 MHz, CDCl3) δ 7.17-7.21 (m, 2 H) 5.76 (s, 1 H) 4.42-4.51 (m, 1 H) 3.91 (s, 3 H) 3.11-3.21 (m, 2 H) 1.60 (d, J=6.57 Hz, 3 H).

Workup

  1. customPurification by flash column chromatography
  2. washeluting with 15-25% EtOAc in hexane

Sources & evidence

ORD record
ord-80c71e788ce742f4827fb9091fa4182e
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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