Tetrahydrofuran → HCID 67794699, compound

HRID 1651068Notes

Reaction equation

HRID 1651068 reaction equation
[Cl:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[CH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.[O:27]1CCCC1>>[Cl:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH:7]([CH2:17][OH:27])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 23051162HCID 23051162, compound

Product 1

HCID 67794699HCID 67794699, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 1-chloro-5-methylene-dibenzo[a,d]cycloheptene (9.0 g) in dry tetrahydrofuran (60 ml), under an inert atmosphere was added 9-borabicyclo[3, 3,1]nonane (80.5 ml of a 0.5 molar solution in THF) at ambient temperature and the reaction mixture was then refluxed for 3h. After cooling, the reaction was quenched by the slow addition of 2N sodium hydroxide solution (180 ml) and 30% hydrogen peroxide (36 ml). After stirring vigorously at 0° C. for 45 minutes the reaction mixture was allowed to warm to room temperature over a 2h period then extracted into diethyl ether (3×250 ml). The combined organic layers were washed with brine (1×500 ml), dried (Na2SO4), filtered and concentrated in vacuo to leave a residue which was purified by chromatography on flash silica with 40% ethyl acetate in hexane as eluent to give the title compound (8.3 g) as a colourless oil. δ (360 MHz, CDCl3) 3.87 (2H, m, CH--CH2OH), 4.21 (1H, t, J=7.9 Hz, CH--CH2OH) 7.02 (1H, d, J=11.9 Hz, CHA =CHB) and 7.17-7.46 (8H, m, CHA =CHB and 7 aromatic protons). m/e 258 and 256 (M+).

Workup

  1. temperaturethe reaction mixture was then refluxed for 3h
  2. temperatureAfter cooling
  3. customthe reaction was quenched by the slow addition of 2N sodium hydroxide solution (180 ml) and 30% hydrogen peroxide (36 ml)
  4. temperatureto warm to room temperature over a 2h period
  5. extractionthen extracted into diethyl ether (3×250 ml)
  6. washThe combined organic layers were washed with brine (1×500 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 40% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-dedc0d124021496e87ae336c597fc493
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

Loading…