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

HRID 1463394

반응식

HRID 1463394 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-9174c5fde683479b9293a27fac732da6
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300522

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