Water → HCID 14502105, compound

HRID 1650377Notes

Reaction equation

HRID 1650377 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:25]([NH:26][C:27](=[O:29])[CH3:28])=[CH:24][CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]=1[OH:30])(C1C=CC(C)=CC=1)(=O)=O.[H-].[Na+].O>C1COCC1.C(OCC)(=O)C>[C:27]([NH:26][C:25]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][O:30][C:17]=2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydride2×HCID 14502104HCID 14502104, compound

Product 1

HCID 14502105HCID 14502105, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 g (14.6 mmol) of methyl 3-(4'-tosyloxybutyl)-4-acetylaminosalicylate in 50 ml of THF is added 0.64 g (16.1 mmol) of sodium hydride (60% dispersion in mineral oil) portionwise at room temperature. After addition is complete stirring is continued 24 hours at room temperature. Water is added dropwise to decompose excess NaH. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated. Flash chromatography (5% EtOAc/hexanes) provides methyl 6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate.

Workup

  1. additionAfter addition
  2. washwashed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c24b7ee132cd4966b8942ab62209f959
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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