Methanol → HCID 20157038, compound

HRID 986700Notes

Reaction equation

HRID 986700 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)=[O:18])=[CH:15][C:14]=2[Br:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43].CO>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:42]([O:34][C:5]1[C:6]([CH2:31][CH2:32][CH3:33])=[C:7]([CH:29]=[CH:30][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[O:18])=[CH:15][C:14]=1[Br:28])(=[O:44])[CH3:43]

Participants

8

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 20157034HCID 20157034, compound

Product 1

HCID 20157038HCID 20157038, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (20 ml) was dissolved tetrahydropyranyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate (1.4 g). To the solution were added triethylamine (6 ml) and 4-dimethylaminopyridine (15 mg), to which was added dropwise acetic anhydride (5 ml) under ice-cooling. The mixture was stirred for 30 minutes under ice-cooling, and there was added methanol (5 ml). The mixture was left standing for a while, and there was added chloroform (50 ml). The mixture was washed with a 5% aqueous solution of sodium hydrogen carbonate and then with water, followed by drying (sodium sulfate). The solvent was evaporated off and the residue was purified by means of a silica-gel column-chromatography to give 3 g of tetrahydropyranyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate as colorless oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitThe mixture was left
  4. washThe mixture was washed with a 5% aqueous solution of sodium hydrogen carbonate
  5. dry with materialby drying (sodium sulfate)
  6. customThe solvent was evaporated off
  7. customthe residue was purified by means of a silica-gel column-chromatography

Sources & evidence

ORD record
ord-a9977c31828a4d6e87f0fb4298544a21
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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