Benzyl Bromide → HCID 89852182, compound

HRID 1771438Notes

Reaction equation

HRID 1771438 reaction equation
[H-].[Na+].[C:3]1([CH3:15])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]([OH:14])[CH2:11][CH:12]=[CH2:13].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([O:14][CH:10]([CH2:11][CH:12]=[CH2:13])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 57677800HCID 57677800, compound

Product 1

HCID 89852182HCID 89852182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (4.9 g, 127.8 mmol) in THF (150 ml) was added 1-o-tolylpent-4-en-2-ol (15 g in THF, 85.22 mmol) at 0° C. stirred for 30 min. Then added benzylbromide (17.85 g, 102.2 mmol) at 0° C. then reaction mixture was stirred for room temperature for 16 h. Then quenched with ice cold H2O and concentrated under reduced pressure to afford crude compound. The title compound was separated by separation method-A and E. (Yield 13.0 g).

Workup

  1. stirringwas stirred for room temperature for 16 h
  2. customThen quenched with ice cold H2O
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude compound
  5. customThe title compound was separated by separation method-A and E

Sources & evidence

ORD record
ord-66930eb3d2ae4d259cb24fa848964d3e
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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