Tetrahydrofuran → HCID 59774920, compound

HRID 2422500Notes

Reaction equation

HRID 2422500 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=[O:16])[C:4]#[C:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[CH2:19]1[CH2:23]OC[CH2:20]1.C([Mg]Cl)C=C.[NH4+].[Cl-]>C(Cl)Cl>[F:18][C:2]([F:1])([F:17])[C:3]([OH:16])([CH2:23][CH:19]=[CH2:20])[C:4]#[C:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:11])[CH3:12])[CH:7]([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 597748871,1,1-Trifluoro-4-(triisopropylsilyl)but-3-yn-2-oneHCID 178418473HCID 178418473, compound

Product 1

HCID 59774920HCID 59774920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-4-(triisopropylsilyl)but-3-yn-2-one (3.00 g, 10.8 mmol) in CH2Cl2 (80 mL) at 0° C., was added a THF solution of allylmagnesium chloride (2.0 M, 8.08 mL, 16.2 mmol). After 1 h, a saturated solution of NH4Cl was added. The aqueous layer was extracted with CHCl3 (3×), and the combined organic layers were washed with H2O and brine, dried (Na2SO4) and concentrated under vacuum at 30° C. affording the title compound (3.63 g). 1H NMR (400 MHz, acetone-d6): 6.02 (m, 2H), 5.20-5.27 (m, 2H), 2.62 (m, 2H), 1.10 (m, 21H).

Workup

  1. extractionThe aqueous layer was extracted with CHCl3 (3×)
  2. washthe combined organic layers were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum at 30° C.

Sources & evidence

ORD record
ord-08643922315d470fb1ad587920aa4846
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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