Sodium Bicarbonate → (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([O:37][C:38](=[O:48])[N:39]([CH3:47])[CH:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:30]([O:37][C:38](=[O:48])[N:39]([CH:40]1[CH2:45][CH2:44][C:43](=[CH:2][O:3][CH3:4])[CH2:42][CH2:41]1)[CH3:47])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A suspension of 749.88 g (2187.5 mmol) (methoxymethyl)triphenylphosphonium chloride in 2.5 l THF was cooled to −10° C. and deprotonated with 245.5 g (2187.5 mmol) potassium t-butoxide. The dark red solution was stirred at 0-5° C. for 0.5 h, cooled to −20° C. and 457.32 g (261.33 mmol) of Methyl-(4-oxo-cyclohexyl)-carbamic acid benzyl ester in 1.251 THF were added over a period of 1.25 h. After 1.3 h at RT, the reaction was treated with 1.75 l aqueous 1M NaHCO3 and stirred for 45 min. The phases were separated, the aqueous phase was extracted with TBME (700 ml), the organic phase was dried (Na2SO4), filtered and evaporated. The residue was suspended in hexane (5 l), cooled (0° C.), filtered and evaporated to give 495.2 g (98%) of (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester, MS: 289 (M).
Workup
- temperaturecooled to −20° C.
- waitAfter 1.3 h at RT
- stirringstirred for 45 min
- customThe phases were separated
- extractionthe aqueous phase was extracted with TBME (700 ml)
- dry with materialthe organic phase was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- temperaturecooled (0° C.)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-27e1c99bce584b5c894d00f0777aac53
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858651B2
Reaction notes
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