Borane;tetrahydrofuran → (RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanol

HRID 394947노트

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HRID 394947 반응식
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:13](O)=[O:14])[CH:10]=2)[S:5][CH2:4][CH2:3]1.B.C1COCC1>C1COCC1>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][OH:14])[CH:10]=2)[S:5][CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 18177798(RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic acid

생성물 1

HCID 18177890(RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanol수율 101.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

0.32 g of (RS)-2-(4,4-dimethyl-thiochroman-6-yl)-heptanoic acid were dissolved in 5 ml THF and treated dropwise, at 0° C., with 5.23 ml of 1M BH3.THF in THF. The mixture was stirred at 0° C. for two hours and then was quenched at 0° C. with careful addition of one portion of 5 ml of 3N HCl. The mixture was stirred at room temperature for 30 min. then was extracted with three portion of 25 ml of ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo, giving a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes), yielding 0.31 g of a colorless oil. 1H NMR (CDCl3): 7.10 (d, J=1.9 Hz, 1H), 6.97 (d, J=8.1 Hz, 1H), 6.81 (dd, J=8.1, 1.9 Hz, 1H), 3.65 (dd, J=10.7, 5.9 Hz, 1H), 3.57 (dd, J=10.7, 8.4 Hz, 1H), 3.00-2.90 (m, 2H), 2.65-2.55 (m, 1H), 1.95-1.85 (m, 2H), 1.65-1.35 (m, 2H), 1.26 (s, 6H), 1.25-1.05 (m, 6H), 0.87 (t, J=7.6 Hz, 3H).

후처리

  1. customwas quenched at 0° C. with careful addition of one portion of 5 ml of 3N HCl
  2. stirringThe mixture was stirred at room temperature for 30 min.
  3. extractionthen was extracted with three portion of 25 ml of ethyl acetate
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customgiving a yellow oil
  7. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-5339328de7cf498daf531223b8646861
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06603012B2

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