Tetrahydrofuran → 2-Cyclopropyl-1,1,1-trifluoro-4-(triisopropylsilyl)but-3-yn-2-ol

HRID 2422498Notes

Reaction equation

HRID 2422498 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.C1([Mg]Br)CC1.[NH4+].[Cl-]>C(Cl)Cl>[CH:20]1([C:3]([OH:16])([C:4]#[C:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:11])[CH3:12])[CH:7]([CH3:8])[CH3:9])[C:2]([F:1])([F:17])[F:18])[CH2:19][CH2:23]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 597748871,1,1-Trifluoro-4-(triisopropylsilyl)but-3-yn-2-oneHCID 178418630HCID 178418630, compound

Product 1

HCID 597749292-Cyclopropyl-1,1,1-trifluoro-4-(triisopropylsilyl)but-3-yn-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-4-(triisopropylsilyl)but-3-yn-2-one (2.01 g, 7.22 mmol) in CH2Cl2 (50 mL) at 0° C. was added a THF solution of cyclopropylmagnesium bromide (0.5 M, 21.7 mL, 10.8 mmol). After 1.5 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. 1H NMR (500 MHz, acetone-d6): 5.97 (s, 1H), 1.36 (m, 1H), 1.10 (m, 21H), 0.74 (m, 1H), 0.65 (m, 2H), 0.60 (m, 1H).

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-f440f647d27a46098f05b906ed1ce315
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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