Water → HCID 19063034, compound

HRID 482511Notes

Reaction equation

HRID 482511 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:26]#[C:27][C:28]4[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH:19]3[CH2:23][O:22]C(C)(C)[O:20]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O>C(O)=O>[C:1]12([C:11]3[CH:12]=[C:13]([C:26]#[C:27][C:28]4[CH:29]=[CH:30][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:36][CH:37]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH:19]([OH:20])[CH2:23][OH:22])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 2

HCID 962WaterHCID 19063044HCID 19063044, compound

Product 1

HCID 19063034HCID 19063034, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

450 mg (0.9 mmol) of methyl 4-[3-(1-adamantyl)-4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl-ethynyl]benzoate were placed in suspension in 10 ml of a formic acid solution (40%) and heated at 100° C. for three days. The reaction mixture was poured into water and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulphate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with dichloromethane. 220 mg (53%) of the expected methyl ester were collected, which ester had the melting point 202°-3° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with dichloromethane
  8. custom220 mg (53%) of the expected methyl ester were collected

Sources & evidence

ORD record
ord-53443f46fd6c423b9cdb1d255dc1634d
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

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