Water → HCID 67958642, compound

HRID 527639Notes

Reaction equation

HRID 527639 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]COC)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67958189HCID 67958189, compound2×

Product 1

HCID 67958642HCID 67958642, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(methoxymethoxy)benzoate (Intermediate 177, 950 mg, 2.68 mmol) was dissolved in dichloromethane (30 ml), the solution was cooled to 0° C. and trifluoroacetic acid (2 ml) was added. After 3 h stirring at 0° C. water (20 ml) was added at 0° C. and two phases were separated. The organic layer was dried over Na2SO4 and evaporated in vacuo to afford a colourless oil that was purified by flash chromatography (Biotage system) on silica gel using cyclohexane to cyclohexane/ethyl acetate 7:3 as eluents affording the title compound (0.345 g) as a colorless oil.

Workup

  1. additionwas added at 0° C.
  2. customtwo phases were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto afford a colourless oil that
  6. customwas purified by flash chromatography (Biotage system) on silica gel

Sources & evidence

ORD record
ord-53dc2431ed9846dc96acc80c0032ae41
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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