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

HRID 394947ノート

反応式

HRID 394947 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5339328de7cf498daf531223b8646861
出典データセット
uspto-grants-2003_08
特許番号
US06603012B2

反応ノート

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