Methanesulfonyl chloride → HCID 20495239, compound

HRID 1074904Notes

Reaction equation

HRID 1074904 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][C:7]1[C:16]2[O:15][CH2:14][CH:13]([CH2:17][OH:18])[CH2:12][C:11]=2[CH:10]=[C:9]([O:19][CH3:20])[CH:8]=1>N1C=CC=CC=1>[OH:6][C:7]1[C:16]2[O:15][CH2:14][CH:13]([CH2:17][O:18][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:12][C:11]=2[CH:10]=[C:9]([O:19][CH3:20])[CH:8]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20495237HCID 20495237, compound

Product 1

HCID 20495239HCID 20495239, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.15 g of mesyl chloride was added to a solution of 6.30 g of 3,4-dihydro-8-hydroxy-3-hydroxymethyl-6-methoxy-2H-1-benzopyran in 90 ml of anhydrous pyridine, and the mixture was stirred for 1.5 hours. After the reaction, the solvent was distilled off. The residue was dissolved in 100 ml of ethyl acetate, and washed with water, 1 N hydrochloric acid and water in this order, and then dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography to give 5.47 g (yield 63.3%) of 3,4-dihydro-8-hydroxy-3-mesyloxymethyl-6-methoxy-2H-1-benzopyran as a pale brown viscous oil.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  4. washwashed with water, 1 N hydrochloric acid and water in this order
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-174f020ce69c493aa26d152674ae14f6
Source dataset
uspto-grants-1983_07
Patent number
US04394382

Reaction notes

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