Triethylamine → 1,2a,4,5,6,6a,7,7a-Octahydrocyclobuta[a]inden-2-one

HRID 2275995

반응식

HRID 2275995 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[CH:10][C:11]([OH:13])=O)[CH:2]=[CH2:3].C(N(CC)CC)C>ClCCl>[CH2:3]1[CH:2]2[CH2:1][CH:4]3[C:5]([CH:10]2[C:11]1=[O:13])=[CH:6][CH2:7][CH2:8][CH2:9]3

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 2785322-(2-Allylcyclohexylidene)acetic acid

생성물 1

HCID 139474001,2a,4,5,6,6a,7,7a-Octahydrocyclobuta[a]inden-2-one수율 83.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-(2-allylcyclohexylidene)acetic acid (800 mg, 4.44 mmol) in dichloromethane (200 mL) was added Ghosez reagent (5.77 mmol, 0.795 mL) at room temperature. The solution was stirred for 45 min until the acid chloride was formed. Then N,N-dimethylaminopyridine (55 mg, 0.45 mmol) was added and the solution was heated to reflux. A solution of triethylamine (8.9 mmol, 1.25 mL) in dichloromethane (3.75 mL) was added dropwise over 30 min. The solution was refluxed for another 1 h and solvent was distilled off. Purification by flash chromatography (pentane/Et2O 95/5) gave 1,2a,4,5,6,6a,7,7a-octahydrocyclobuta[a]inden-2-one (600 mg, 83%) as a colourless liquid, with 20% of the tetrasubstituted regioisomere. 1H NMR (400 MHz, CDCl3) 5.59 (1H, brs), 3.92 (1H, brs), 3.21 (1H, dddd), 2.92 (1H, m), 2.73 (1H, m), 2.51 (1H, m), 2.04 (4H, m), 1.79 (1H, m), 1.48 (2H, m), 1.05 (1H, m).

후처리

  1. customwas formed
  2. temperaturethe solution was heated to reflux
  3. temperatureThe solution was refluxed for another 1 h
  4. distillationsolvent was distilled off
  5. customPurification by flash chromatography (pentane/Et2O 95/5)

출처 및 근거

ORD 기록
ord-2d33d8b10de54dcb9df9bf62cac0c033
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09131688B2

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