2-Methyl-3-butyn-2-ol → Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-

HRID 1393309Notes

Reaction equation

HRID 1393309 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].[Si:7](OS(C(F)(F)F)(=O)=O)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C(Cl)Cl>[C:10]([Si:7]([O:6][C:2]([CH3:3])([CH3:1])[C:4]#[CH:5])([CH3:9])[CH3:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate2×

Product 1

HCID 11084826Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-Yield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-but-3-yn-2-ol (2.20 g, 26.2 mmol) in DCM (50 mL) was mixed with 2,6-lutadine (9.1 mL, 78.6 mmol). TBSOTf (6.6 mL, 28.8 mmol) was added to the reaction mixture slowly. After 2 hours at room temperature, an extra amount of TBSOTf (1.5 mL) was added. After 16 hours at room temperature, the reaction was quenched with 10% HOAc aqueous solution (400 mL). The product was extracted with DCM (2×200 mL). The combined organic layers were washed with brine, dried and concentrated. Purification of the crude on silica gel column (Foxy, 3:7 EtOAc/Hexane) provided desired product as colorless liquid (4.12 g, 80%). 1H NMR (CDCl3) δ 2.58 (s, 1H), 0.82 (s, 6H).

Workup

  1. waitAfter 16 hours at room temperature
  2. customthe reaction was quenched with 10% HOAc aqueous solution (400 mL)
  3. extractionThe product was extracted with DCM (2×200 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification of the crude on silica gel column (Foxy, 3:7 EtOAc/Hexane)

Sources & evidence

ORD record
ord-fb63598edcd94565914f755cdd34fdb5
Source dataset
uspto-grants-2008_03
Patent number
US07345084B2

Reaction notes

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