Tetrahydrofuran → HCID 67794549, compound

HRID 1651071Notes

Reaction equation

HRID 1651071 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[C:7](=[CH2:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:5]=2[CH:4]=1.C12BC(CCC1)CCC2.C1C[O:31]CC1>>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[CH:7]([CH2:16][OH:31])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 23051190HCID 23051190, compound

Product 1

HCID 67794549HCID 67794549, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methoxy-5-methylene-dibenzo [a,d]cycloheptene (12.8 g) in dry THF (50 ml), under an inert atmosphere, was added 9-borabicyclo[3,3,1]nonane (116 ml of a 0.5 molar solution in THF) at ambient temperature, and the reaction mixture was then refluxed for 3h. After cooling in an ice bath the reaction was quenched by the slow addition of 2N sodium hydroxide solution (150 ml) and 30% hydrogen peroxide (30 ml). After stirring vigorously at 0° C. for 45 minutes the reaction mixture was allowed to warm to room temperature over a period of 2h then extracted with diethyl ether (3×200 ml). The combined organic layers were washed with brine (1×300 ml), dried (Na2SO4), filtered and concentrated in vacuo to leave a residue, which was purified by chromatography on flash silica with 30% ethyl acetate in hexane as eluent, to give the title compound (10.9 g) as an oil. δ(360 MHz, CDCl3) 3.77-3.81 (2H, d, J=8.1 Hz, CH2), 3.80 (3H, s, OCH3), 4.16 (1H, t. J=8.1 Hz, CH--CH2OH), 6.79 (1H, d, J=11.9 Hz, ArCHA =CHB --Ar), 6.33 (1H, d, J=2.6 Hz, CH=C(OCH3)--CH), 6.85 (1H, d, J=11.9 Hz, Ar--CHA =CHB --Ar), 6.89 (1H, dd, J=8.3 and 2.6 Hz, CH=C(OCH3)CH) and 7.23-7.33 (5H, m, aromatics). m/e (CI+) 253 (M+1).

Workup

  1. temperaturethe reaction mixture was then refluxed for 3h
  2. temperatureAfter cooling in an ice bath the reaction
  3. customwas quenched by the slow addition of 2N sodium hydroxide solution (150 ml) and 30% hydrogen peroxide (30 ml)
  4. temperatureto warm to room temperature over a period of 2h
  5. extractionthen extracted with diethyl ether (3×200 ml)
  6. washThe combined organic layers were washed with brine (1×300 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto leave a residue, which
  11. customwas purified by chromatography on flash silica with 30% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-45c98c63fcd94bbbb3d2c90eae477604
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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