Water → 5,6-Difluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)indene-3-acetic acid

HRID 610097Notes

Reaction equation

HRID 610097 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=2)[CH2:7][C:6]=1[CH3:16].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O.O>N1C=CC=CC=1>[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[F:15])[C:7](=[CH:23][C:22]1[CH:21]=[C:20]([O:19][CH3:18])[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=1)[C:6]([CH3:16])=[C:5]2[CH2:4][C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 68583,4,5-TrimethoxybenzaldehydeHCID 12052144Methyl 5,6-difluoro-2-methylindene-3-acetate

Product 1

HCID 541353805,6-Difluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)indene-3-acetic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.19 g (5.0 mmol) of 5,6-difluoro-2-methylindene-3-acetic acid methyl ester is dissolved in 10 ml of dry pyridine followed by 0.98 g (5.0 mmol) of 3,4,5-trimethoxy-benzaldehyde. The flask is placed under nitrogen, and 5.0 g (5.1 mol) of Triton B is added. The deeply colored solution is allowed to stand overnight, and then water (2 ml) is added. After standing for 15 minutes, it is poured into an excess of water. The organics are extracted with ether (2×50 ml). The aqueous phase is added to 10% HCl-ice. The orange, gummy solid that precipitates is extracted into methylene chloride and dried (MgSO4). The solvent is removed to leave an orange solid. The solid is filtered to give a crude product which is recrystallized to give 5,6-difluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)indene-3-acetic acid. When 2,4,6-trimethoxybenzaldehyde or 2,4,5-trimethoxybenzdehyde is utilized in the above procedure, instead of 3,4,5--trimethoxy-benzaldehyde, the corresponding indene acetic acid is obtained. (R and R1 =H, R2 and R3 =F, R4 =H, R5, R6 and R7 =OCH3, R8 =CH3, o=1, M=OH)

Workup

  1. addition5.0 g (5.1 mol) of Triton B is added
  2. waitAfter standing for 15 minutes
  3. extractionThe organics are extracted with ether (2×50 ml)
  4. additionThe aqueous phase is added to 10% HCl-ice
  5. extractionThe orange, gummy solid that precipitates is extracted into methylene chloride
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed
  8. customto leave an orange solid
  9. filtrationThe solid is filtered
  10. customto give a crude product which
  11. customis recrystallized

Sources & evidence

ORD record
ord-7e554d3807654061888563b68342826a
Source dataset
uspto-grants-1999_12
Patent number
US05998477

Reaction notes

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