Trifluoroacetic acid → HCID 13671288, compound

HRID 1478160Notes

Reaction equation

HRID 1478160 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[O:15]1[C:19]2([CH2:29][CH2:28][C:22]3([CH2:26][CH2:25][O:24][CH:23]3O)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:15]1[C:19]2([CH2:29][CH2:28][C:22]3([CH2:26][CH2:25][O:24][CH2:23]3)[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 118511097HCID 118511097, compound

Product 1

HCID 13671288HCID 13671288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of triethylsilane (1.965 mL, 12.30 mmol) in DCM (40 mL), under nitrogen, at −78° C. was successively added trifluoroacetic acid (0.948 mL, 12.30 mmol) and [1,4,10-trioxadispiro[4.2.4.2]tetradecan-9-ol](0.878 g, 4.1 mmol) in DCM (40 mL) at −78° C. The resulting mixture was slowly warmed to 0° C. and stirred for 2 hours. Saturated aqueous NaHCO3 solution was added and the mixture was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound.

Workup

  1. customat −78° C.
  2. customat −78° C
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a4ebcb5f9ade4c38a04d63889c3d549f
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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