Iodine chloride → HCID 67318946、化合物

HRID 132401

反応式

HRID 132401 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[I:22]Cl>CO.ClCCl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([I:22])=[C:11]([CH:10]=1)[CH2:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 24640Iodine chlorideHCID 743413-(Phenylmethoxy)benzenemethanolHCID 516892Sodium Bicarbonate

生成物 1

HCID 67318946HCID 67318946、化合物収率 71%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a well stirred solution of 3-benzyloxybenzyl alcohol (5.5 g, 25.7 mmol) in methanol (100 mL) and sodium hydrogencarbonate (8.4 g, 100 mmol) was added a 1.0 M solution of iodine monochloride in dichloromethane (30 mL) at 0° C. The reaction mixture was brought to room temperature and stirring continued for additional 1 h. The reaction mixture was concentrated and then diluted with dichloromethane (150 mL), washed with 10% aqueous sodium thiosulfate and dried (Na2SO4). The desired compound was purified by flash chromatography (silica) using 20% ethyl acetate in hexane to give 5-benzyloxy-2-iodobenzyl alcohol (6.2 g, 71% yield). The alcohol (4.2 g, 12.4 mmol) was dissolved in dichloromethane (100 mL) added acetic anhydride (2.52 g, 24.7 mmol) and catalytic amount of 4-dimethylaminopyridine. The reaction mixture was then stirred for 12 h, washed with aqueous sodium hydrogencarbonate and then dried (Na2SO4) to give acetic acid 5-benzyloxy-2-iodo-benzyl ester in quantitative yield. MS (ESI) 405 (M+Na) ; Rf=2.27.

後処理

  1. customwas brought to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with dichloromethane (150 mL)
  4. washwashed with 10% aqueous sodium thiosulfate
  5. dry with materialdried (Na2SO4)
  6. customThe desired compound was purified by flash chromatography (silica)

出典と根拠

ORDレコード
ord-38a2f4600c934643bbd17c1c9aff6d30
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

関連ノート

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