Benzyl Bromide → cis-4-Benzyloxy-2-buten-1-ol

HRID 595325Notes

Reaction equation

HRID 595325 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([OH:14])[CH:10]=[CH:11][CH2:12][OH:13].[H-].[Na+]>CN(C=O)C.[Cl-].[NH4+]>[CH2:1]([O:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 80652-Butene-1,4-diolHCID 24758Sodium hydride

Product 1

HCID 11008492cis-4-Benzyloxy-2-buten-1-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Benzyl bromide (8.0 g, 47 mmol) was added over a period of 30 minutes to a mixture of but-2-ene-1,4-diol (25.0 g, 281 mmol) and sodium hydride (2.2 g, 94 mmol) in DMF (100 mL) at 0° C. The mixture was stirred for 16 hours at room temperature. The mixture was then diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (methanol/ethyl acetate) to afford (2Z)-4-(benzyloxy)but-2-en-1-ol. 1H NMR (400 MHz, CD3OD) δ 7.34-7.27 (m, 5H), 5.75-5.64 (m, 2H), 4.50 (s, 2H), 4.12-4.09 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product residue
  6. customThe crude product residue was purified by silica gel chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-c6a367095c7f415a92dc8fbeb83bd29b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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