Diethyl Ether → HCID 69507241, compound

HRID 2181748Notes

Reaction equation

HRID 2181748 reaction equation
[Cl:1][C:2]([Cl:19])([Cl:18])[CH2:3][O:4][C:5]([O:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH2:17])C=O)[N:13]=1)=[O:6].[CH3:20][CH2:21][CH2:22]CC.[C:25]([O-:28])(O)=O.[Na+].[CH3:30]COCC>>[OH:28][C@H:25]([C:17]([CH3:30])=[CH:14][C:12]1[N:13]=[C:9]([CH2:8][O:7][C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:18])[Cl:19])=[O:6])[S:10][CH:11]=1)[CH2:22][CH:21]=[CH2:20]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8003PentaneHCID 516892Sodium BicarbonateHCID 131723665HCID 131723665, compound

Product 1

HCID 69507241HCID 69507241, compound

Conditions

Temperature
-50 °C

Procedure

A solution of 2-methyl-3-(2-((2,2,2-trichloroethoxycarbonyloxymethyl)thiazol-4-yl)propenal (9.20 g) in 50 mL of anhydrous ether is cooled to −100° C. A pentane solution of (+)-diisopinocampheylallylborane (1.5 equiv) is added dropwise to the vigorously stirred aldehyde solution. After the addition is complete, the reaction mixture is stirred for 1.5 hours and warmed to −50° C. A solution of 30% aq H202 (20 mL) and 10% aq NaHCO3 (50 mL) is added, and the resulting turbid mixture is stirred at 25° C. for 8 hours. The organic layer is separated, and the aqueous layer is extracted with ether. The combined organic layers are washed with satd aq Na2S2O3 and brine, dried (MgSO4), filtered, and concentrated. Purification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 10:1) affords the alcohol as a clear oil (7.65 g).

Workup

  1. additionAfter the addition
  2. stirringthe resulting turbid mixture is stirred at 25° C. for 8 hours
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with ether
  5. washThe combined organic layers are washed with satd aq Na2S2O3 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-30d9fb93039f4e05bfa962ebbaae99f6
Source dataset
uspto-grants-2005_05
Patent number
US06893859B2

Reaction notes

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