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Ethyl 4-oxocyclohexanecarboxylate → HCID 18340695, compound

HRID 714511
Notes
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Reaction equation

HRID 714511 reaction equation
[Cl-].[Li+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.O=[C:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1>CC#N>[C:15]([O:14][C:12](=[O:13])[CH:11]=[C:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1)([CH3:16])([CH3:17])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 433294Lithium ChlorideHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 18340695HCID 18340695, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of anhydrous lithium chloride (1.9 g, 45 mmol) in MeCN (100 ml) was added tert-butyl 2-(diethoxyphosphoryl)acetate (7.6 g, 30 mmol) at room temperature. The mixture was stirred for 30 min. TEA (6.4 ml, 45 mmol) was added and the mixture was stirred for another 30 min. Ethyl 4-oxocyclohexanecarboxylate (5.1 g, 30 mmol) was added and the mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1) to afford product (5 g, 62%).

Workup

  1. stirringthe mixture was stirred for another 30 min
  2. stirringthe mixture was stirred overnight
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto afford brown oil, which
  6. customwas purified by silica gel column (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-d6bc09e0770f4cd694958a3123fba500
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187447B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes