Trifluoroacetic acid → HCID 21082633, compound

HRID 347318Notes

Reaction equation

HRID 347318 reaction equation
O[CH:2]([C:10]1[C:19]([O:20][CH3:21])=[CH:18][C:17]2[C:16]([CH3:23])([CH3:22])[CH2:15][CH2:14][C:13]([CH3:25])([CH3:24])[C:12]=2[CH:11]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[O:9])[O:6][CH:7]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][O:20][C:19]1[C:10]([CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[O:9])[O:6][CH:7]=2)=[CH:11][C:12]2[C:13]([CH3:25])([CH3:24])[CH2:14][CH2:15][C:16]([CH3:22])([CH3:23])[C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21082650HCID 21082650, compound

Product 1

HCID 21082633HCID 21082633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 4-[hydroxy(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furaldehyde (2.9 g, 8.5 mmol), triethylsilane (2.9 g, 25.4 mmol) and anhydrous methylene chloride (40 mL) was cooled to 0° C. To this mixture was added trifluoroacetic acid (˜1.0 mL, 8.5 mmol) and the reaction was allowed to stir at RT for 16 hours. The reaction was quenched with saturated NaHCO3 and the organics were separated and dried over MgSO4. The resulting oil (2.5 g) was used without further purification.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. customthe organics were separated
  3. dry with materialdried over MgSO4
  4. customThe resulting oil (2.5 g) was used without further purification

Sources & evidence

ORD record
ord-10554eca9f58495182eabb4233710506
Source dataset
uspto-grants-2007_02
Patent number
US07173134B2

Reaction notes

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