2,6-Lutidine → HCID 57890084, compound

HRID 1819940Notes

Reaction equation

HRID 1819940 reaction equation
[CH2:1]([C:3]([C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][CH:18]([OH:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:14]([CH3:26])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2].CC1C=CC=C(C)N=1.FC(F)(F)S(O[Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])(=O)=O>ClCCl>[CH2:1]([C:3]([C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][CH:18]([O:23][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[C:19]([CH3:21])([CH3:20])[CH3:22])=[C:14]([CH3:26])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 57890137HCID 57890137, compound

Product 1

HCID 57890084HCID 57890084, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-ol (7.5 g, 20 mmol) in dichloromethane (100 ml) at −78° C. is added 2,6-dimethylpyridine (5.8 ml, 50 mmol) followed by tert-butyldimethylsilyl trifluoromethanesulfonate (6.0 ml, 26 mmol). After stirring at RT for 2 h, the reaction diluted with dichoromethane and washed successively with 1N HCl followed by satd NaHCO3. The organic layer is dried over MgSO4 and concentrated to give the title product (9.5 g, 97%).

Workup

  1. washwashed successively with 1N HCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3830d1bc017d4850bc84ef9291861344
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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