Water → HCID 14650424, compound

HRID 1199914Notes

Reaction equation

HRID 1199914 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C:4]([OH:7])([CH3:6])[CH3:5].O([Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])S(C(F)(F)F)(=O)=O.N1C(C)=CC=CC=1C.O>C(Cl)Cl>[Si:17]([O:7][C:4]([CH3:6])([CH3:5])[C:3]([O:2][CH3:1])=[O:8])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 75024Methyl alpha-hydroxyisobutyrateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 14650424HCID 14650424, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, chilled (0° C.) solution of methyl-2-hydroxyisobutyrate (20.0 g) in dry CH2Cl2 was added TBDMS triflate (45 g) dropwise, followed by anhydrous 2,6-lutidine (19.3 g). The mixture was stirred at 0° C. for 1 hour before 150 ml water was added. Stirring was continued for a further hour, the organic layer separated, dried (Na2SO4), and concentrated to dryness at reduced pressure. The crude product was purified by dry flash silica gel chromatography eluting with CH2Cl2 to yield the title compound as a colorless oil (30.9 g). δH (360 MHz, CDCl3) 0.07 (6H, s, Si(CH3)2), 0.87 (9H, s, C(CH3)3), 1.41 (6H, s, C(CH3)2), 3.69 (3H, s, CH3O). m/z 233 (M+1)+, 100%, CI+) 217 (30), 174 (40), 164 (45), 106 (30).

Workup

  1. additionwas added
  2. waitwas continued for a further hour
  3. customthe organic layer separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness at reduced pressure
  6. customThe crude product was purified
  7. customby dry flash silica gel chromatography
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-c21fd946a0ea42eeafc51b46e2044daf
Source dataset
uspto-grants-1990_02
Patent number
US04904654

Reaction notes

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