2,6-Lutidine → HCID 16732673, compound

HRID 1363831Notes

Reaction equation

HRID 1363831 reaction equation
N1C(C)=CC=CC=1C.[C:9]([O:17][C@@H:18]([CH3:39])[C:19](=[O:38])[C@H:20]([CH3:37])[C@H:21]([OH:36])/[C:22](/[CH3:35])=[CH:23]/[CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Si:40](OS(C(F)(F)F)(=O)=O)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41].C(=O)([O-])O.[Na+]>ClCCl>[C:9]([O:17][C@@H:18]([CH3:39])[C:19](=[O:38])[C@H:20]([CH3:37])[C@H:21]([O:36][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])/[C:22](/[CH3:35])=[CH:23]/[CH2:24][O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 12000446HCID 12000446, compound

Product 1

HCID 16732673HCID 16732673, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2,6-Lutidine (38.2 ml, 328 mmol) was added to an anhydrous dichloromethane (1.00 l) solution of (1S,3R,4S,5E)-4-hydroxy-7-[(4-methoxybenzyl)oxy]-1,3,5-trimethyl-2-oxohept-5-en-1-yl benzoate (70.0 g, 164 mmol) at −78° C. under nitrogen atmosphere. Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester (56.5 ml, 246 mmol) was added dropwise to the reaction solution over 10 minutes. After the reaction solution was stirred at −78° C. for one and a half hour, a saturated sodium hydrogen carbonate aqueous solution was added at −78° C. The reaction solution was warmed to room temperature, which was then extracted with dichloromethane. After the organic layer was washed with water and brine sequentially, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=8:1) to obtain the title compound (89.0 g) as a colorless oil.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. extractionwhich was then extracted with dichloromethane
  3. washAfter the organic layer was washed with water and brine sequentially
  4. dry with materialit was dried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-46e9bf594ade43898ce158eabc73623f
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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