HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Bicarbonate → (4R,5S,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,4,6-tetramethyl-8-nonenal

HRID 2296860
Notes
Print preview

Reaction equation

HRID 2296860 reaction equation
C([O:4][CH:5](OC(C)C)[C:6]([CH3:27])([CH3:26])[C:7](=[O:25])[C@H:8]([CH3:24])[C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[O:25]=[C:7]([C@H:8]([CH3:24])[C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])[C:6]([CH3:27])([CH3:26])[CH:5]=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86586616HCID 86586616, compound

Product 1

HCID 11211787(4R,5S,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,4,6-tetramethyl-8-nonenal

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (4R,5S,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,4,6-tetramethyl-8-nonen-3-one (4.58 g) and p-toluenesulfonic acid monohydrate (0.45 g) in 100 mL of 3:1 THF/water is heated at reflux for 7 hours. The mixture is cooled and poured into sat. aq. NaHCO3, then extracted with ethyl acetate. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2 (3% ethyl acetate/hexanes).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product is purified by chromatography on SiO2 (3% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-54cd16a208f34be5bfe118b59653425f
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06489314B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes