Acetic Acid → HCID 53967837, compound

HRID 2399802Notes

Reaction equation

HRID 2399802 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[C:14]3[C:15]4[CH:21]=[CH:20][C:19](O)=[CH:18][C:16]=4[NH:17][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H-].[Na+].[N+]([C:28]1[O:32][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:30][CH:29]=1)([O-])=O.C(O)(=[O:39])C>CS(C)=O.O>[CH3:36][O:35][C:33]([CH:31]1[CH2:30][CH2:29][CH:28]([O:39][C:12]2[CH:11]=[CH:10][CH:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:14]3[C:13]=2[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=32)[O:32]1)=[O:34]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 94882Methyl 5-nitro-2-furoateHCID 19384529HCID 19384529, compound2×

Product 1

HCID 53967837HCID 53967837, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of approximately 7.25 mmol of 5,6,7,8-tetrahydro-9-[(4-fluorophenyl)methyl]-9H-dibenzo[b,d]pyrrol-3-ol as a crude oil from Example 100 in 20 ml of dimethyl sulfoxide was added dropwise to a freshly prepared suspention of 0.35 g of sodium hydride (55% dispersion in mineral oil) in 2 ml dimethylsulfoxide at room temperature and under argon. The resulting mixture was stirred an additional 15 minutes and a solution of methyl 5-nitro-2-furoate (1.37 g) in dimethylsulfoxide (10 mL) was added. The black mixture was stirred an additional 2 hours and poured into ice and water containing a few drops of acetic acid. The product was extracted with dichloromethane and the organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by HPLC eluting with ethyl acetate-hexane (1:9) and crystallized from ether-hexane. 2.2 g (72%) of 1,2,3,4-tetrahydro-5-[[9-[(4-fluorophenyl)methyl]-9H-dibenzo[b,d]pyrrol-6-yl]oxy] -2-furancarboxylic acid methyl ester was obtained as a colorless crystalline material, mp 85°-86° C.

Workup

  1. stirringThe black mixture was stirred an additional 2 hours
  2. extractionThe product was extracted with dichloromethane
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by HPLC
  7. washeluting with ethyl acetate-hexane (1:9)
  8. customcrystallized from ether-hexane

Sources & evidence

ORD record
ord-e573dfe004e644ef80c1d55bc34dc767
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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