Water → HCID 67260803, compound

HRID 2378511Notes

Reaction equation

HRID 2378511 reaction equation
[CH3:1][CH:2]1[CH2:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:17])[CH2:3]1.N(CCCC)(CCCC)CCCC.O>C(Cl)Cl.C(OCCCC)(C)=O>[OH:17][C:4]12[CH2:3][CH:2]([CH3:1])[CH2:15][C:14](=[O:16])[CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 7622TributylamineHCID 595502923-Methylcyclotetradecane-1,5-dione

Product 1

HCID 67260803HCID 67260803, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31272Butyl AcetateSolvent

Procedure

A solution of 3-methyl-1,5-cyclotetradecanedione 29 (500 mg, 2.1 mmol) in CH2Cl2 (4 ml) was treated at 22-24° C. with a solution of ZrCl3OPr (36% in AcOBu) (1.79 g, 3.86 mmol). After 15 minutes the solution was treated at −10° C. with NBu3 (0.68 g, 0.88 ml, 3.68 mmol). After 70 minutes, the reaction mixture was poured into 5 ml water and 7 ml of a aqueous 2 NHC1 solution were added. After extraction with 25 ml diethyl ether the combined organic phases were washed (saturated aqueous NaHCO3 solution, H2O), dried (Na2SO4) and the solvent was evaporated (crude 531 mg). Flash chromatography, using SiO2 (25 g) and n-pentane/diethyl ether=6:4 as eluent, afforded 364 mg (yield: 73%) of (30).

Workup

  1. additionwere added
  2. extractionAfter extraction with 25 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 531 mg)

Sources & evidence

ORD record
ord-f9caeedfa9b346048387d74e0bef4b0a
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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