Tetrahydrofuran → HCID 15735694, compound

HRID 1885551Notes

Reaction equation

HRID 1885551 reaction equation
CCCCCCCCC.[CH2:10]([O:17][CH:18]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:19][CH:20]=[CH2:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O:39]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][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:19][CH2:20][CH2:21][OH:39])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8141NonaneHCID 15735693HCID 15735693, compound

Product 1

HCID 15735694HCID 15735694, compoundYield 78%

Procedure

To a 33 ml solution of a 0.5M solution of 9-borabicyclo[3:3:1]nonane in tetrahydrofuran was added dropwise, under nitrogen, a solution of 6.0 g of 4-benzyloxy-1-heneicosene in 30 ml of dry tetrahydrofuran. After stirring at room temperature for 3 hours, the reaction was quenched by successive addition of 9 ml of ethanol, 3 ml of 6N sodium hydroxide and 6.5 ml 30% hydrogen peroxide. The reaction mixture was heated at 50° for 90 minutes and then allowed to stand at ambient temperature overnight. Upon standing, the reaction mixture separated into aqueous and organic phases. The aqueous phase was saturated with potassium carbonate, and the organic phase was separated, washed with 15 ml of 10% solution of sodium sulfite and 20 ml of saturated solution of sodium chloride, dried over potassium carbonate, and concentrated. The residue was taken up in a mixture of 20% diethyl ether/hexane, filtered and concentrated to an oil. Flash chromatography of the oil on silica gel using hexane/diethyl ether (2:1 by volume) as the eluent gave 4.88 g (78%) of 4-benzyloxyheneicosan-1-ol.

Workup

  1. customthe reaction was quenched by successive addition of 9 ml of ethanol, 3 ml of 6N sodium hydroxide and 6.5 ml 30% hydrogen peroxide
  2. temperatureThe reaction mixture was heated at 50° for 90 minutes
  3. waitto stand at ambient temperature overnight
  4. customthe reaction mixture separated into aqueous and organic phases
  5. customthe organic phase was separated
  6. washwashed with 15 ml of 10% solution of sodium sulfite and 20 ml of saturated solution of sodium chloride
  7. dry with materialdried over potassium carbonate
  8. concentrationconcentrated
  9. additionThe residue was taken up in a mixture of 20% diethyl ether/hexane
  10. filtrationfiltered
  11. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-612a8a8597844c22bedcb988e6230978
Source dataset
uspto-grants-1992_09
Patent number
US05145844

Reaction notes

Loading…