Benzyl 4-Hydroxybenzoate → Benzyl 4-(4,4-dimethyl-6-thiochromanoyloxy)benzoate

HRID 330337Notes

Reaction equation

HRID 330337 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1.O[C:17]1[CH:32]=[CH:31][C:20]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][C:17]3[CH:32]=[CH:31][C:20]([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])=[CH:19][CH:18]=3)=[O:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 10868DicyclohexylcarbodiimideHCID 198342284,4-Dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-carboxylic acid

Product 1

HCID 19834230Benzyl 4-(4,4-dimethyl-6-thiochromanoyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 786 mg (3.54 mmol) of 4,4-dimethyl-6-carboxythiochroman, 804 mg (3.53 mmol) of benzyl 4-hydroxybenzoate, 800 mg (3.88 mmol) of 1, 3-dicyclohexylcarbodiimide and 60 mg (0.49 mmol) of 4-dimethylaminopyridine in 50 ml of methylene chloride was stirred at room temperature for 2 hours. The reaction mixture was then filtered and the residue washed with 20 ml of methylene chloride. The filtrate was concentrated in-vacuo and the resultant crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexanes) followed by recrystallization from a mixture of hexanes and ethyl acetate to give the title compound as a white, crystalline solid. PMR (CDCl3): δ1.39 (6H, s), 1.98 (2H, m), 3.08 (2H, m), 5.37 (2H, s), 7.20 (1H, d, J~8.3 Hz), 7.28 (2H, d, J~8.0 Hz), 7.34-7.48 (5H, m), 7.82 (1H, dd, J~8.3, 2.0 Hz), 8.14 (2H, d, J~8.0 Hz),

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe residue washed with 20 ml of methylene chloride
  3. concentrationThe filtrate was concentrated in-vacuo
  4. customthe resultant crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexanes)
  5. customfollowed by recrystallization from a mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-32f498d6c256451faaf7f6b274cbcc57
Source dataset
uspto-grants-1990_01
Patent number
US04895868

Reaction notes

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