tert-Butanol → t-Butyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate

HRID 2177783Notes

Reaction equation

HRID 2177783 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([S:22]([CH2:25][C:26]2[C:31]([C:32]([OH:34])=[O:33])=[C:30]([OH:35])[C:29]([C:36]3[CH:40]=[CH:39][O:38][CH:37]=3)=[CH:28][CH:27]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:41](O)([CH3:44])([CH3:43])[CH3:42]>C1COCC1.CN(C)C1C=CN=CC=1>[C:16]1([S:22]([CH2:25][C:26]2[C:31]([C:32]([O:34][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:33])=[C:30]([OH:35])[C:29]([C:36]3[CH:40]=[CH:39][O:38][CH:37]=3)=[CH:28][CH:27]=2)(=[O:24])=[O:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 52914186HCID 52914186, compound2×

Product 1

HCID 67107716t-Butyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dicyclohexylcarbodiimide (0.124 g) in THF (1 ml) was added dropwise to a mixture of 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoic acid (Intermediate 114, 0.358 g) and 4-dimethylaminopyridine (0.0032 g) and t-butanol (3 ml) in THF (1 ml). The resultant mixture was stirred at room temperature for 4 hours. The solid was removed by filtration and the filtrate was washed with citric acid (5% aqueous solution), sodium bicarbonate (saturated aqueous solution) and brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (20%) to give t-butyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (0.19 g) as a waxy white solid.

Workup

  1. customThe solid was removed by filtration
  2. washthe filtrate was washed with citric acid (5% aqueous solution), sodium bicarbonate (saturated aqueous solution) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (20%)

Sources & evidence

ORD record
ord-bec010efc15f4e8383fd30b87179434e
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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