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

HRID 1590705Notes

Reaction equation

HRID 1590705 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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]

Sources & evidence

ORD record
ord-83315bfa2bab43258aa7b1171131fcc0
Source dataset
uspto-grants-1993_04
Patent number
US05204373

Reaction notes

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