Hydrochloric Acid → HCID 68826874, compound

HRID 2378513Notes

Reaction equation

HRID 2378513 reaction equation
[CH3:1][CH:2]1[CH2:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:19])[CH2:3]1.N(CCCC)(CCCC)CCCC.O.Cl>C(Cl)Cl.C(OCCCC)(C)=O>[OH:19][C:4]12[CH2:3][CH:2]([CH3:1])[CH2:17][C:16](=[O:18])[CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7622TributylamineHCID 595502973-Methylcyclohexadecane-1,5-dione

Product 1

HCID 68826874HCID 68826874, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31272Butyl AcetateSolvent

Procedure

A solution of 3-methyl-1,5-cyclohexadecanedione (33) (1 g, 3.76 mmol) in CH2Cl2 (6 ml) was treated at 22-24° with a solution of ZrCl3OPr (36% in AcOBu) (3 g, 5.0 mmol). After 15 minutes the solution was treated at −10° C. with NBu3 (1.15 g, 1.48 ml, 6.2 mmol). After 60 minutes, the reaction mixture was poured into 15 ml water and 15 ml of a 2 N HCl solution were added. After extraction with 50 ml diethyl ether the combined organic phases were washed (saturated aqueous NaHCO3 solution, H2O), dried (Na2SO4) and the solvent was evaporated (crude 1.0 g). Flash chromatography, using SiO2 (100 g) and n-pentane/diethyl ether=6:4 as eluent, afforded 898 mg (yield: 90%) of (34).

Workup

  1. additionwere added
  2. extractionAfter extraction with 50 ml diethyl ether the combined organic phases
  3. washwere washed (saturated aqueous NaHCO3 solution, H2O)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated (crude 1.0 g)

Sources & evidence

ORD record
ord-b65ae9566f9748c18e73d9f0e411523f
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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