Water → HCID 18185234, compound

HRID 1358541Notes

Reaction equation

HRID 1358541 reaction equation
[CH3:1][Mg]Cl.[O:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[CH2:7][CH2:6][CH2:5]1.O.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:8]1([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 18185234HCID 18185234, compoundYield 119.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution [sic], maintained under an inert atmosphere, of 33.5 ml (0.1 mol) of 3M methylmagnesium chloride in solution in tetrahydrofuran is heated to 50° C. 11.3 g (0.069 mol) of 3,4-dihydro-2H-benzoxepin-5-one, dissolved in 150 ml of tetrahydrofuran, are added fairly quickly. This solution is brought to reflux for 4 hours and is then left stirring overnight at room temperature. The reaction mixture is subsequently gently hydrolysed with water under cold conditions. An ammonium chloride solution (120 g per litre) is then poured into the reaction mixture. The latter is extracted with ethyl acetate and then the organic phase is dried over anhydrous sodium sulphate and concentrated under reduced pressure. 14.7 g of a yellow oil are obtained, which oil is purified by crystallization from isoctane. 11.9 g of the title compound are thus obtained, the melting point of which is 92° C.

Workup

  1. additionare added fairly quickly
  2. temperatureto reflux for 4 hours
  3. waitis then left
  4. extractionThe latter is extracted with ethyl acetate
  5. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c63f77a6ce7c43b58699b93bd9c5982a
Source dataset
uspto-grants-2003_07
Patent number
US06596758B1

Reaction notes

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