Tetrahydrofuran → HCID 15735700, compound

HRID 1885553Notes

Reaction equation

HRID 1885553 reaction equation
C12BC(CCC1)CCC2.[CH2:10]([O:17][CH:18]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:19][CH:20]=[CH2:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O:37]1CCCC1>>[CH2:10]([O:17][CH:18]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:19][CH2:20][CH2:21][OH:37])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 15735699HCID 15735699, compound

Product 1

HCID 15735700HCID 15735700, compoundYield 75%

Procedure

To a 0.5M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (253 ml) was added dropwise, under nitrogen, a solution of 41.8 g of 4-benzyloxy-13-phenyl-1-tridecene in 100 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 3 hours, quenched by the sequential addition of 72 ml of ethanol, 24 ml of 6 N solution of sodium hydroxide, and 48 ml of a 30% solution of hydrogen peroxide. The mixture was heated at 50° for 2.5 hours. Upon standing at room temperature overnight, the mixture separated into aqueous and organic layers. The organic layer was washed with 100 ml of a 10% aqueous solution of sodium sulfite and 100 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous potassium carbonate and concentrated. The concentrate was taken up in 20% diethyl ether/hexane, filtered and concentrated to an oil. The oil was purified by high pressure liquid chromatography using as an eluent hexane/diethyl ether (2:1 by volume) to give 32.7 g (75%) 4-benzyloxy-13-phenyl-tridecan-1-ol as an oil.

Workup

  1. customquenched by the sequential addition of 72 ml of ethanol, 24 ml of 6 N solution of sodium hydroxide, and 48 ml of a 30% solution of hydrogen peroxide
  2. temperatureThe mixture was heated at 50° for 2.5 hours
  3. waitUpon standing at room temperature overnight
  4. customthe mixture separated into aqueous and organic layers
  5. washThe organic layer was washed with 100 ml of a 10% aqueous solution of sodium sulfite and 100 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated
  8. filtrationfiltered
  9. concentrationconcentrated to an oil
  10. customThe oil was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-9c08f1f69f714502a785ff2b868c6e95
Source dataset
uspto-grants-1992_09
Patent number
US05145844

Reaction notes

Loading…