Carbon tetrabromide → Cis-1-Bromo-tetradec-6-ene

HRID 1925764

반응식

HRID 1925764 반응식
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 6431339(Z)-6-Tetradecen-1-ol

생성물 1

HCID 58641109Cis-1-Bromo-tetradec-6-ene수율 70.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Alcohol 7 (115 mg, 0.541 mmol) in dichloromethane (100 ml) at 0° C. was treated successively with carbon tetrabromide (395 mg, 1.20 mmol) and triphenylphosphine (312 mg, 1.20 mmol), and allowed to warm to room temperature with stirring over 2 h. The reaction mixture was triturated with water and extracted with methylene chloride, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography using hexanes as an eluent, thus affording pure 8 as a light oil (105 mg, 0.381 mmol, 70%); δH(270 MHz, CDCl3); 0.87 (3H, t, J=6.1 Hz), 1.1-1.65 (14H, m), 1.85 (2H, quin, J 7.0), 2.03 (4H, m), 3.4 (2H, t, J 6.8) and 5.35 (4H, m); δC(67.5 MHz, CDCl3) 27.06, 27.32 27.72, 27.91, 28.04, 28.96, 29.32, 29.37, 29.71, 29.83, 31.96, 32.82, 34.01, 129.31, 130.47.

후처리

  1. customThe reaction mixture was triturated with water
  2. extractionextracted with methylene chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-5e14b8b7ff6a4c158480bfecaae9297b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178713B2

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