Diethyl Ether → HCID 20570498, compound

HRID 262144Notes

Reaction equation

HRID 262144 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:25])[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([OH:24])=[CH:9][CH:10]=2)[O:5]1.Cl[CH2:27][C:28]#[N:29].CCOCC>CN(C)C=O>[C:28]([CH2:27][O:24][C:8]1[CH:7]=[C:6]2[C:11]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[CH:15]=3)[CH2:13][C:4]([CH3:25])([CH3:3])[O:5]2)=[CH:10][CH:9]=1)#[N:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 20570489HCID 20570489, compound

Product 1

HCID 20570498HCID 20570498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.93 g, 80% dispersion in oil) was added to a solution of 2,2-dimethyl-4-(3-trifluoromethylphenyl)chroman-7-ol (containing 1 mole of carbon tetrachloride of crystallisation) (7.5 g) in dimethylformamide (25 ml). Chloroacetonitrile (1.76 g) was added and the mixture heated at 60° C. for 3 hours. The solvent was removed under reduced pressure and the resulting oil was poured into water. The aqueous solution was extracted with ether and the etheeal extracts were dried (MgSO4) and evaporated under reduced pressure to yield an oil. Chromatography on alumina with ether--petrol (40°-60° C.), 1:3 as eluate gave the title compound which crystallised on standing.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe resulting oil was poured into water
  3. extractionThe aqueous solution was extracted with ether
  4. dry with materialthe etheeal extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto yield an oil

Sources & evidence

ORD record
ord-d49e0aad9f3640058485e2ec8d0379d6
Source dataset
uspto-grants-1979_05
Patent number
US04153617

Reaction notes

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