Sodium hydride → HCID 86703673, compound

HRID 1849791Notes

Reaction equation

HRID 1849791 reaction equation
[C:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H-].[Na+].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>CN(C)C=O>[C:1]1([CH2:7][O:8][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 317542(Cyclohex-1-en-1-yl)methanol

Product 1

HCID 86703673HCID 86703673, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of cyclohexenylmethanol (2.50 g, 22.3 mmol) in N,N-dimethylformamide (40 mL) and sodium hydride (60% dispersion in mineral oil, 0.89 g, 22.3 mmol) was added in portions at 0° C. The reaction mixture was stirred for 0.5 hour, then added 1-(chloromethyl)-4-methoxybenzene (3.49 g, 22.3 mmol). The reaction mixture was stirred for another 0.5 hour and quenched with slow addition of water (50 mL). The organic layer was extracted with ethyl acetate (80 mL) and concentrated in vacuo to dryness. The residue was purified by column chromatography with ethyl acetate in hexanes (10%) to afford the title compound as a colorless liquid (3.50 g, 68%).

Workup

  1. additionwas added in portions at 0° C
  2. stirringThe reaction mixture was stirred for another 0.5 hour
  3. customquenched with slow addition of water (50 mL)
  4. extractionThe organic layer was extracted with ethyl acetate (80 mL)
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography with ethyl acetate in hexanes (10%)

Sources & evidence

ORD record
ord-6bd366707a9f478da6ff6f48c3b47a8e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…