Hydrochloric Acid → HCID 22221603, compound

HRID 1836056Notes

Reaction equation

HRID 1836056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[O:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.C[Si]([C:26]([F:29])([F:28])[F:27])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[F:27][C:26]([F:29])([F:28])[CH:20]([C:5]1[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[CH:8][C:7]=2[CH:19]=[C:3]([O:2][CH3:1])[CH:4]=1)[OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 10308280HCID 10308280, compound

Product 1

HCID 22221603HCID 22221603, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 (1.2 g, 4.3 mmol) and Trimethylsilyltrifluoromethane (20 ml of 0.5M in THF, 10 mmol) in THF (20 ml) was added TBAF (10 ml of 1.0M in THF, 10 mmol) and the reaction was stirred at rt. After 30 min, the rextion was poured into 2N HCl and extracted with ether. The ether was dried, concentrated and the product was purified by column chromatography (eluent 10% EtOAc/Hex) to give 139 as a solid (1.2 g, 80%); Mp=120-122° C.; 1H NMR(CDCl3) δ 7.75 (d, 2 H, J=8.8 Hz), 7.15-6.95 (m, 4 H), 6.84 (s, 1 H), 5.59 (m, 1 H), 3.86 (s, 6 H); MS 353 (M+H)+

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether was dried
  3. concentrationconcentrated
  4. customthe product was purified by column chromatography (eluent 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-cb99801dd49944bbbbfb0ef02f720c35
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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