4-Toluenesulfonyl chloride → HCID 131719473, compound

HRID 55367Notes

Reaction equation

HRID 55367 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][OH:12].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1.C1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][OH:12].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O-:22])(=[O:1])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27948162-(Hydroxymethyl)chroman

Product 1

HCID 131719473HCID 131719473, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (0° C.) solution of 32.8 g of 3,4-dihydro-2H-1-benzopyran-2-methanol in 71 ml of pyridine and 135 ml of benzene was added dropwise a solution of 41.9 g of 4-methyl-benzenesulfonyl chloride in 72.5 ml of benzene. Upon completion, stirring was continued for 25 hours. The reaction mixture was washed successively with a hydrochloric acid solution (10%), with water and with a sodium carbonate solution (10%). The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 100%). The eluent of the desired fraction was evaporated, yielding 28.3 g of 3,4-dihydro-2H-1-benzopyran-2-methanol 4-methylbenzenesulfonate (ester) as a solid residue, mp. 59.4° C. (interm. 1). In a similar way there was also prepared: 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol 4-methylbenzenesulfonate (ester) (interm. 2).

Workup

  1. stirringUpon completion, stirring
  2. washThe reaction mixture was washed successively with a hydrochloric acid solution (10%), with water and with a sodium carbonate solution (10%)
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CHCl3 100%)
  7. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-5b9f29fe823a448489c6bb602c1e96d2
Source dataset
uspto-grants-1997_04
Patent number
US05624952

Reaction notes

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