Ethyl orthoformate → 3-Bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol

HRID 929110

反応式

HRID 929110 の反応式
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.[OH:13][CH2:14][C:15]([CH3:19])([CH2:17]O)[CH3:16].C(OCC)(OCC)OCC>CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:7]([CH:8]2[O:13][CH2:14][C:15]([CH3:19])([CH3:17])[CH2:16][O:9]2)=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 31344Neopentyl glycolHCID 2622376-Bromo-2-hydroxy-3-methoxybenzaldehyde

生成物 1

HCID 597618363-Bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol収率 100%

試薬・触媒・溶媒 1

HCID 6101p-Toluenesulfonic acid触媒

反応条件

温度
110 °C

実験手順

A mixture of 6-bromo-2-hydroxy-3-methoxy-benzaldehyde (2.31 g, 10.0 mmol), neopentyl glycol (1.14 g, 11.0 mmol), TsOH (9.5 mg) and triethyl orthoformate (1.93 g, 13.0 mmol) were heated at 110° C. for 30 min and then partitioned between NaHCO3 (300 mL) solution and EtOAc (200 mL). The aqueous layer was extracted with EtOAc (3×30 mL) and the combined extracts were washed with brine and dried through Na2SO4. Evaporation of solvent afforded the title compound (3.17 g, 100%). 1H NMR (CDCl3) δ 0.85 (s, 3H), 1.27 (s, 3H), 3.70 (s, 2H), 3.82 (s, 2H), 3.85 (s, 3H), 5.90 (s, 1H), 6.72 (d, J=8 Hz, 1H), 7.02 (d, J=8 Hz, 1H).

後処理

  1. custompartitioned between NaHCO3 (300 mL) solution and EtOAc (200 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried through Na2SO4
  5. customEvaporation of solvent

出典と根拠

ORDレコード
ord-c1ede8de17c641598a8aca29cbf778de
出典データセット
uspto-grants-2016_03
特許番号
US09290503B2

関連ノート

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