Triethylamine → 4-Hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

HRID 1643708Notes

Reaction equation

HRID 1643708 reaction equation
[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:12]=[C:11]([O:13]CC2C=CC=CC=2)[C:10]([CH2:21][C:22]2([CH3:25])[CH2:24][O:23]2)=[C:9]([O:26]CC2C=CC=CC=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC>CO.[Pd]>[C:1]([O:5][C:6]([C:7]1[CH:12]=[C:11]([OH:13])[C:10]2[CH2:21][C:22]([CH2:24][OH:23])([CH3:25])[O:26][C:9]=2[CH:8]=1)=[O:34])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 595604243,5-Bis-benzyloxy-4-(2-methyl-oxiranylmethyl)-benzoic acid tert-butyl ester

Product 1

HCID 595599054-Hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl esterYield 18.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,5-bis-benzyloxy-4-(2-methyl-oxiranylmethyl)-benzoic acid tert-butyl ester (227b) (158 g, 0.343 mol), 10% Pd/C (15 g), Et3N (57.3 mL, 0.412 mol) and K2Co3 (56.94 g, 0.412 mol) in MeOH (1.5 L) was stirred under 760 mmHg of H2 at room temperature overnight. TLC (EtOAc/petroleum ether=1/3) showed that 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 a brown oil. The brown oil was further purified by prep. HPLC to give the title compound (18 g, 18.7% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.98 (s, 1H), 6.82(s, 1H), 3.67 (d, 1 H), 3.56 (d, 1H), 2.80 (d, 1H), 1.48 (s, 9H), 1.35 (s, 3H).

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)
  4. customto give a brown oil
  5. customThe brown oil was further purified by prep

Sources & evidence

ORD record
ord-f2d3a06b5db842a9b0824d21f57846ff
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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