Water → 4-Chloro-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 344770Notes

Reaction equation

HRID 344770 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8](O)[C:7]=2[CH:15]=1)#[N:2].C(N(CC)CC)C.CS([Cl:27])(=O)=O.O>ClCCl>[Cl:27][CH:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110090196-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol

Product 1

HCID 537676584-Chloro-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol (U.K. Patent Application GB 2 204 868A) (2.93 g) and triethylamine (4.04 ml) in dichloromethane (100 ml) was added methanesulphonylchloride (2.24 ml) over 30 min, under an atmosphere of nitrogen. The reaction mixture was stirred for 18 h, water was added and the organic phase separated, washed with aqueous sodium hydrogencarbonate and dried over anhydrous sodium sulphate. Filtration and evaporation of the solvent in vacuo gave the title compound (3.03g) as a solid, which was used in the next step without further purification.

Workup

  1. customthe organic phase separated
  2. washwashed with aqueous sodium hydrogencarbonate
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationFiltration and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-4e17afd236b34c4b953cd66af90cdfe2
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

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