Water → HCID 19812452, compound

HRID 373390Notes

Reaction equation

HRID 373390 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH:17]=[O:18])=[C:11]([CH3:19])[C:10]=1[CH:20]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC1C=CC=CC=1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:43]>O1CCOCC1.[Ag]=O>[CH2:1]([CH:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([C:10]1[C:11]([CH3:19])=[C:12]([C:17]([OH:43])=[O:18])[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[C:26]([OH:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 15125145HCID 15125145, compound

Product 1

HCID 19812452HCID 19812452, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution benzyl 7-(2-benzyloxy-5-formyl-3,4,6-trimethylphenyl)-7-(4-fluorophenyl)heptanoate (2.3 g) in dioxane (20 ml) and water (2 ml) was added silver oxide (II) (4.5 g) and the mixture was stirred for 12 days. Insoluble materials were filtered off and washed with ethyl acetate. The washing was combined with the filtrate and the mixture was concentrated. Ethyl acetate was added and the mixture was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to obtain benzyl 7-(2-benzyloxy-5-carboxy-3,4,6-trimethylphenyl)-7-(4fluorophenyl)heptanoic acid (1.5 g) (Compound 68). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. filtrationInsoluble materials were filtered off
  2. washwashed with ethyl acetate
  3. concentrationthe mixture was concentrated
  4. additionEthyl acetate was added
  5. washthe mixture was washed with water and saturated saline
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dad41b02e33d42abb9a71508093b8e20
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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