Triethylamine → tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylate

HRID 1177195Notes

Reaction equation

HRID 1177195 reaction equation
[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[C:11]([O:13]CC2C=CC=CC=2)[C:10]([CH2:21][CH:22]2[CH2:24][O:23]2)=[C:9]([O:25]CC2C=CC=CC=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>CO.[Pd]>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([OH:25])[C:10]2[CH2:21][CH:22]([CH2:24][OH:23])[O:13][C:11]=2[CH:12]=1)=[O:33])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 595602363,5-Bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester

Product 1

HCID 25067321tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylateYield 56.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,5-bis-benzyloxy-4-oxiranylmethyl-benzoic acid tert-butyl ester (200e) (55 g, 0.12 mol), 10% Pd on Carbon (5 g), Et3N (15 g, 0.14 mol), and K2CO3 (20 g, 0.14 mol) in MeOH (250 mL) was stirred under 760 mmHg of H2 at room temperature for 4 hr. TLC (EtOAc/petroleum oil=1/2) showed the reaction was complete. The mixture was filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (EtOAc/petroleum ether=1/3) to give the title compound (18 g, 55% yield) as an off-white solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography (EtOAc/petroleum ether=1/3)

Sources & evidence

ORD record
ord-e69a0d534c174f34ae9971081836ad23
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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