2,6-Lutidine → 4-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide

HRID 1948161Notes

Reaction equation

HRID 1948161 reaction equation
[CH3:1][O:2][N:3]([CH3:17])[C:4]([C:6]1([C:13]([F:16])([F:15])[F:14])[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])(=O)=O>C(Cl)Cl>[CH3:1][O:2][N:3]([CH3:17])[C:4]([C:6]1([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:10][CH:9]([O:12][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 583808584-Hydroxy-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide

Product 1

HCID 583808694-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.00 g (23.5 mmol) of 4-Hydroxy-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide (69) were dissolved in 20 ml of CH2Cl2 and 6.8 ml of 2,6-lutidine were added. Afterwards, 6.48 ml (28.2 mmol) of tert-butyldimethylsilyl trifluoromethanesulfonate were added at 0° C. and the mixture allowed to stand at ambient temperature for 16 h. The mixture was then diluted using 30 ml of CH2Cl2 and washed successively twice using 30 ml of water, twice using 30 ml of a 0.1; N aqueous HCl-solution and once using 30 ml of a saturated aqueous NaHCO3-solution respectively. The organic layer was then dried over MgSO4 and evaporated to yield 8.40 g. Rt=0.99 min (Method Q).

Workup

  1. additionThe mixture was then diluted
  2. washwashed successively twice
  3. dry with materialThe organic layer was then dried over MgSO4
  4. customevaporated
  5. customto yield 8.40 g

Sources & evidence

ORD record
ord-e62e57189b114bc6885db32f9b1f3301
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

Loading…