Triethylamine → (1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 407840

反応式

HRID 407840 の反応式
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:13]2[CH:8]([CH:9]3[O:14][CH:12]2[CH2:11][CH2:10]3)[C:7](=[O:15])[CH:6]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:6]1[C:7](=[O:15])[CH:8]2[CH:13]([C:5]=1[O:4][CH3:3])[CH:12]1[O:14][CH:9]2[CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24408BromineHCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

生成物 1

HCID 67283643(1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of bromine (0.14 ml, 2.8 mmol) in dichloromethane (5 ml) is added dropwise to a solution of the enol ether (0.48 g, 2.6 mmol) prepared in step 1 in dichloromethane (40 ml) at 0° C. and the reaction mixture is stirred for 1 hour. Triethylamine (0.64 ml, 4.6 mmol) is then added and the reaction mixture is allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture is washed with 2M aqueous hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one.

後処理

  1. stirringstirred for 3 hours
  2. washThe reaction mixture is washed with 2M aqueous hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-13fc2705a1474372abe61736e60ceacd
出典データセット
uspto-grants-2014_06
特許番号
US08754242B2

関連ノート

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