Iodine → 2,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

HRID 373549

反応式

HRID 373549 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.II.[O:15]1CC[CH2:17][CH2:16]1>BrCCBr>[CH3:17][CH:16]([C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1)[OH:15]

参加物

5

反応物 3

HCID 807IodineHCID 8028TetrahydrofuranHCID 199355348-Bromo-2,3,4,5-tetrahydrobenzo[b]oxepine

生成物 1

HCID 199354272,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

試薬・触媒・溶媒 1

HCID 78391,2-Dibromoethane触媒

反応条件

温度
-10 °C

実験手順

7.3 g of 8-bromo-2,3,4,5-tetrahydro-1-benzoxepine in 30 ml of absolute tetrahydrofuran were added under argon to 930 mg shavings and a granule of iodine. The reaction was intitiated by the addition of a few drops of 1,2-dibromoethane and has finished after 2 hours. Thereafter, the reaction mixture was cooled to -10° C. and excess acetaldehyde was distilled into the reaction vessel. After 10 minutes, the mixture was hydrolyzed with saturated sodium bicarbonate (NaHCO3) solution, extracted with ether, washed with water, dried and evaporated to dryness. Chromatography on silica gel (petroleum ether/ethyl acetate 3:1) yielded 4.93 g of 2,3,4,5-tetrahydro-α-methyl-1-benzoxepine-8-methanol as a colorless oil.

後処理

  1. distillationexcess acetaldehyde was distilled into the reaction vessel
  2. waitAfter 10 minutes
  3. extractionextracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-c8c67de915d2404f9289478b5992c195
出典データセット
uspto-grants-1992_11
特許番号
US05164387

関連ノート

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