Benzyl Bromide → HCID 69046728, compound

HRID 1821543Notes

Reaction equation

HRID 1821543 reaction equation
[H-].[Na+].[CH3:3][C@H:4]([OH:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.C(OCC)(=O)C.O1CCCC1>[CH2:14]([O:13][C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[CH3:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 71351475HCID 71351475, compound

Product 1

HCID 69046728HCID 69046728, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3.2 g (133 mmol) sodium hydride (freed from paraffin) in 105 ml ice cold abs. tetrahydrofuran was added 6.2 g (39.5 mmol) (S)-dec-9-ene-2-ol under argon. After stirring for 2 h, 470 mg (1.3 mmol) tetra-n-butyl ammonium iodide were added, followed by dropwise addition of 13.5 g (9.4 ml, 78.9 mmol) benzyl bromide, while stirring was continued for 12 h. Subsequently, 50 ml saturated aqueous ammonium chloride solution were added at 0° C. followed by 50 ml hexane. The aqueous layer was separated and extracted four times with 100 ml of a 1:4 mixture of ethyl acetate/hexane. The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. Flash chromatography (5% ethyl acetate in hexane furnished 9.7 g (39.4 mmol, 100%) (S)-2-benzyloxydec-9-ene.

Workup

  1. stirringwhile stirring
  2. waitwas continued for 12 h
  3. customThe aqueous layer was separated
  4. extractionextracted four times
  5. additionwith 100 ml of a 1:4 mixture of ethyl acetate/hexane
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12a62f0a53d44fbc8f2efbd0b8f72793
Source dataset
uspto-grants-2009_10
Patent number
US07608254B2

Reaction notes

Loading…