Allyl bromide → HCID 23567780, compound

HRID 1797335Notes

Reaction equation

HRID 1797335 reaction equation
[C:1]([O:20][CH2:21][C@@H:22]([OH:35])[CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][C:37](C)([O-])[CH3:38].[K+].C(Br)C=C>C1COCC1.CCCCCC>[C:1]([O:20][CH2:21][C@@H:22]([O:35][CH2:38][CH:37]=[CH2:36])[CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 67528372HCID 67528372, compound

Product 1

HCID 23567780HCID 23567780, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of Compound 5 (10 grams, 21.4 mmoles) in dry THF (250 ml), a solution of 1M of potassium t-butoxide (Aldrich) (27.8 ml, 27.8 mmoles) in THF was added, under argon atmosphere. The mixture was stirred at room temperature for 5 minutes and, thereafter, allyl bromide (Aldrich) (7.4 ml, 85.5 mmoles) was added. The mixture was stirred for 18 hours at 55° C. The solvent was thereafter evaporated to dryness and the residue was extracted with ethyl acetate (250 ml) and washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting yellowish oily residue was purified by silica gel chromatography, using 1:2 (v:v) ethyl acetate:hexane as eluent, 10.75 grams (99% yield) of Compound 6 were obtained as an oil.

Workup

  1. stirringThe mixture was stirred for 18 hours at 55° C
  2. customThe solvent was thereafter evaporated to dryness
  3. extractionthe residue was extracted with ethyl acetate (250 ml)
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting yellowish oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb18c9ac444d4c82ae48dd9566d99864
Source dataset
uspto-grants-2006_04
Patent number
US07034131B2

Reaction notes

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