Methyl p-toluenesulfonate → HCID 9825819, compound

HRID 375131Notes

Reaction equation

HRID 375131 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1([CH3:19])[CH2:10][CH2:9][C:8]2[C:11]([CH3:18])=[C:12]([OH:17])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:30]C)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[CH2:32](OC(=O)C)C>C(#N)C>[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1.[OH:17][C:12]1[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]2[O:6][C:5]([CH2:4][CH2:3][S+:2]([CH3:32])[CH3:1])([CH3:19])[CH2:10][CH2:9][C:8]=2[C:11]=1[CH3:18]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 8857Ethyl AcetateHCID 10423809HCID 10423809, compound

Product 1

HCID 9825819HCID 9825819, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.90 g of 3,4-dihydro-2-(2-methylthioethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol and 2.12 g (10% excess) of methyl 4-methylbenzenesulfonate in 30 ml of acetonitrile is refluxed for 48 hours. On cooling and addition of ethylacetate, the product crystallizes and is recrystallized from the same solvent pair, 4.19 g (87% yield), m.p. 156°-158° C., identified by elemental analysis, IR, UV and 1H and 13C NMR spectra.

Workup

  1. temperatureOn cooling
  2. customthe product crystallizes
  3. customis recrystallized from the same solvent pair, 4.19 g (87% yield), m.p. 156°-158° C.

Sources & evidence

ORD record
ord-441a36a5664c43f988fa639a8d77124e
Source dataset
uspto-grants-1996_01
Patent number
US05484810

Reaction notes

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