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

HRID 37412

반응식

HRID 37412 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 78391,2-Dibromoethane촉매

반응 조건

온도
-10 °C

실험 절차

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 of Mg shavings and a granule of iodine. The reaction was initiated by the addition of a few drops of 1,2-dibromoethane and had 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.

후처리

  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

출처 및 근거

ORD 기록
ord-69558ce886804b19993bb5e130032ad6
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420273

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