Triphenylphosphine → methyl 7-(benzenesulfonylmethyl)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778342Notes

Reaction equation

HRID 1778342 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]1([S:21]([CH2:24][C:25]2[C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:29](O)[C:28]([C:36]3[CH:40]=[CH:39][O:38][C:37]=3[CH:41]([OH:43])[CH3:42])=[CH:27][CH:26]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]1([S:21]([CH2:24][C:25]2[C:30]([C:31]([O:33][CH3:34])=[O:32])=[C:29]3[C:28]([C:36]4[CH:40]=[CH:39][O:38][C:37]=4[CH:41]([CH3:42])[O:43]3)=[CH:27][CH:26]=2)(=[O:22])=[O:23])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66685568Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-[2-(1-hydroxyethyl)-furan-3-yl]-benzoate2×

Product 1

HCID 66685680methyl 7-(benzenesulfonylmethyl)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.02 g) was added to a solution of methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-[2-(1-hydroxyethyl)-furan-3-yl]-benzoate (Intermediate 20, 0.042 g) and triphenylphosphine (0.026 g) in THF (2 mL) and the mixture was stirred for 1 hour. The mixture 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 5-10% to give methyl 7-(benzenesulfonylmethyl)-4-methyl-4H-furo[2,3-c]chromene-6-carboxylate (0.038 g) as a white solid.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-10%

Sources & evidence

ORD record
ord-881471c1a1964eb2aa66d196f89565d2
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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