Water → HCID 66592760, compound

HRID 548976Notes

Reaction equation

HRID 548976 reaction equation
C([C:3]1([C:19]([O-:21])=[O:20])[O:7][C:6]2=[C:8]([O:16]C)[CH:9]=[CH:10][C:11](C)([C:12]([O-:14])=[O:13])[C:5]2=[C:4]1[CH3:18])C.CN(C)P(=O)(N(C)C)N(C)C.O.[C:34]1(C)C=CC=C[CH:35]=1>>[CH2:34]([O:21][C:19]([C:3]1[O:7][C:6]2[C:8]([OH:16])=[CH:9][CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:5]=2[C:4]=1[CH3:18])=[O:20])[CH3:35]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 12679HexamethylphosphoramideHCID 86636830HCID 86636830, compound

Product 1

HCID 66592760HCID 66592760, compound

Procedure

The solution of 2-ethyl-4-methyl-7-methoxy-3-methylbenzo[b]furan-2,4-dicarboxylate (from step 5 of example 1) (13.0 g), sodium p-thiocresolate (20.26 g, 1.5 equiv.) and hexamethylphosphoric acid triamide (24.80 g, 1.5 equiv.) was heated in dry toluene at reflux temperature under nitrogen for 2-6 h. The reaction mixture was cooled to room temperature, water was added and aqueous layer was washed with dichloromethane. Aqueous layer was acidified at 10-15° C. with concentrated hydrochloric acid. The precipitated product was filtered and dried.

Workup

  1. temperatureat reflux temperature under nitrogen for 2-6 h
  2. washaqueous layer was washed with dichloromethane
  3. customwas acidified at 10-15° C. with concentrated hydrochloric acid
  4. filtrationThe precipitated product was filtered
  5. customdried

Sources & evidence

ORD record
ord-949524138cc74aeca26ca02cd16df443
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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