Water → tert-butyl 7-(benzenesulfonylmethyl)-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778341Notes

Reaction equation

HRID 1778341 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([S:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:36]=[CH:35][O:34][C:33]=3[C:37]([OH:39])=[O:38])=[C:28](O)[C:27]=2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]1([S:22]([CH2:25][C:26]2[C:27]([C:41]([O:43][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:42])=[C:28]3[C:29]([C:32]4[CH:36]=[CH:35][O:34][C:33]=4[C:37](=[O:39])[O:38]3)=[CH:30][CH:31]=2)(=[O:23])=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 666926633-[4-(Benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid2×

Product 1

HCID 66685941tert-butyl 7-(benzenesulfonylmethyl)-4-oxo-4H-furo[2,3-c]chromene-6-carboxylateYield 137.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N,N′-dicyclohexylcarbodiimide (0.014 g) was added to a solution of 3-[4-(benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid (Intermediate 21, 0.028 g) and DMAP (0.0003 g) in DCM (5 mL) and the mixture was stirred for 72 hours. Water and DCM were added and the organic layer was separated, dried (MgSO4) 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 with a gradient of 30-40% to give tert-butyl 7-(benzenesulfonylmethyl)-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate (0.037 g) as a white solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-40%

Sources & evidence

ORD record
ord-bd6935a6b3874373b41641c422cb9ff2
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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