Sodium Bicarbonate → 3-Octanone

HRID 433952

Reaction equation

HRID 433952 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[C:13](=O)(O)[O-].[Na+]>C(Cl)Cl.COCOC>[CH3:13][CH2:3][C:4](=[O:1])[CH2:5][CH2:6][CH2:7][CH2:2][CH3:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2467283-Octanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8020DimethoxymethaneSolvent

Procedure

To a solution of 6(7)-hydroxy-2-methoxycarbonyl-8-azabicyclo(3.2.1)octane-3-one (18 g, 84.5 mmol) in 200 ml of CH2Cl2, 70 ml of dimethoxymethane was added, followed by (18 g, 93 mmol) of p-toluene sulfonic acid monohydrate. The round-bottom flask was fitted with a soxhiet extractor containing 3-4 A molecular sieves. The reaction mixture was heated to reflux with stirring until the starting material had disappeared (TLC). The mixture was cooled and treated with sat. sodium bicarbonate solution and extracted with CH2Cl2. The combined organics were dried over K2CO3 removed in vacuo and applied to column (silica gel, 10% Et3N, 30% EtOAc/hexane). 6-Methoxymethoxy-2-methoxy-carbonyl-8-azabicyclo(3.2.1))octane-3-one (2.2 g) was obtained as a yellow oil. Rf 0.3 (10% Et3N, 30% EtOAc in hexane).

Workup

  1. customThe round-bottom flask was fitted with a soxhiet extractor
  2. additioncontaining 3-4 A molecular sieves
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperatureThe mixture was cooled
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined organics were dried over K2CO3
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-3bf54d0d810949f38dce6c07a261bb88
Source dataset
uspto-grants-2003_12
Patent number
US06670375B2

Linked notes

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