Tetrahydrofuran → HCID 58958432, compound

HRID 915165Notes

Reaction equation

HRID 915165 reaction equation
C1COCC1.[Cl:6][CH:7]([Si](C)(C)C)[Cl:8].Cl.CO.[F:16][C:17]([F:28])([F:27])[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23]>C(OCC)C.O>[Cl:6][CH:7]([Cl:8])[CH:22]([C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][C:17]([F:16])([F:27])[F:28])[CH:20]=1)[OH:23]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 80026Silane, (dichloromethyl)trimethyl-HCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 21893726Hydrochloride methanol

Product 1

HCID 58958432HCID 58958432, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared as outlined in JACS, 1985, 107, 4085-4087 as follows. A 1.0M THF solution of 19-2 (0.19 g, 1.0 mmol) was added to a THF solution (2 mL) of (dichloromethyl) trimethylsilane 19-6 (0.188 g, 1.2 mmol) and 19-5 (0.9 g, 0.25 mmol) and stirred at room temperature for 18 hours. The reaction was then treated with 300 μL (0.3 mmol) of 1N HCl/MeOH for 20 minutes and diluted with ethyl ether and water. The ether was removed, dried with sodium sulfate, filtered and evaporated to afford a 4:1 mixture of 19-7 and 3-(trifluoromethoxy)benzaldehyde. This was used without further purification.

Workup

  1. customThe ether was removed
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford
  6. customThis was used without further purification

Sources & evidence

ORD record
ord-4e08c9e5ab7c4dd8b2c7378eaabfa105
Source dataset
uspto-grants-2007_09
Patent number
US07265134B2

Reaction notes

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