Borane → (6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

HRID 1590705ノート

反応式

HRID 1590705 の反応式
[OH:1][CH:2]=[C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]1=O.B.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:14][O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][CH:3]([CH2:2][OH:1])[CH2:12][CH2:11]2

参加物

5

反応物 3

HCID 6331BoraneHCID 8000Boron trifluoride etherateHCID 2643163,4-Dihydro-2-(hydroxymethylene)-6-methoxy-1(2H)-naphthalenone

生成物 1

HCID 10058404(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Hydroxymethylene-6-methoxy-1-tetralone (2) (4.81 g, 0.024 mole) and borane:t-butylamine complex (10.25 g, 0.12 mole) were dissolved in about 250 mL of methylene chloride and the solution was cooled to about -78°. Boron trifluoride etherate (14.5 mL, 0.12 mole) was added dropwise and the mixture was stirred for about 1 hour then warmed to about 23° and stirred for an additional 2 hours. The reaction mixture was quenched with about 1N HCl and extracted with methylene chloride. The methylene chloride extracts were dried (MgSO4) and concentrated in vacuo. The crude oil was purified by flash chromatography [gradient 3:1 to 1:2 Hexanes:Ether] to yield the title compound as a light yellow oil (3.41 g, 0.018 mole, 75% yield): IR (Film) 3362, 2996, 2918, 1610, 1504, 1464, 1264, 1234, 1040 cm-1 ; 1H NMR (CDCl3) δ1.40 (m, 1H), 1.47 (s, 1H), 1.95 (m, 2H), 1.39,1.45 (d of d, J=10.6,16.1 Hz, 1H), 2.81 (m, 2H), 3.62 (d, J=6.3 HZ, 2H), 3.77 (s, 3H), 6.62 (d, J=2.6 Hz, 1H), 6.68 (d of d, J=8.4,2.6 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H); MS m/e 193 (MH+).

後処理

  1. temperaturethe solution was cooled to about -78°
  2. temperaturethen warmed to about 23°
  3. stirringstirred for an additional 2 hours
  4. customThe reaction mixture was quenched with about 1N HCl
  5. extractionextracted with methylene chloride
  6. dry with materialThe methylene chloride extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified by flash chromatography [gradient 3:1 to 1:2 Hexanes:Ether]

出典と根拠

ORDレコード
ord-83315bfa2bab43258aa7b1171131fcc0
出典データセット
uspto-grants-1993_04
特許番号
US05204373

反応ノート

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