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

HRID 1177195

反応式

HRID 1177195 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e69a0d534c174f34ae9971081836ad23
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

関連ノート

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