Trifluoroacetic acid → HCID 21082656, compound

HRID 347319Notes

Reaction equation

HRID 347319 reaction equation
O[CH:2]([C:11]1[CH:20]=[CH:19][C:18]2[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:9]=[O:10])[O:6][C:7]=1[CH3:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:8][C:7]1[O:6][C:5]([CH:9]=[O:10])=[CH:4][C:3]=1[CH2:2][C:11]1[CH:20]=[CH:19][C:18]2[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21082651HCID 21082651, compound

Product 1

HCID 21082656HCID 21082656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 4-[hydroxy-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-5-methyl-2-furaldehyde (3.6 g, 11 mmol), triethylsilane (3.8 g, 33.1 mmol) and anhydrous methylene chloride (50 mL) was cooled to 0° C. To this mixture was added trifluoroacetic acid (˜1.3 g, 11.4 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 was used without further purification (the product appears to quickly decompose).

Workup

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

Sources & evidence

ORD record
ord-2340995c64dd46198e28a5ae13665b34
Source dataset
uspto-grants-2007_02
Patent number
US07173134B2

Reaction notes

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