Diisopropyldichlorosilane → HCID 13431539, compound

HRID 2206820Notes

Reaction equation

HRID 2206820 reaction equation
Cl[Si:2]([Cl:9])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[CH2:10]([Li])[CH2:11][CH2:12][CH3:13]>O1CCCC1>[CH2:10]([Si:2]([CH:3]([CH3:4])[CH3:5])([CH:6]([CH3:7])[CH3:8])[Cl:9])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 2758384DiisopropyldichlorosilaneHCID 178418339Butyllithium

Product 1

HCID 13431539HCID 13431539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dichlorodiisopropylsilane 1 is treated with n-butyllithium in tetrahydrofuran solution to yield butyldiisopropyl-chlorosilane 2, which is then reacted with lithium (trimethylsilyl)acetylide in situ to yield trimethylsilyl protected ethynyl butyldiisopropylsilane 3. Selective removal of the TMS group with potassium carbonate affords ethynyl butyldiisopropylsilane 4. Using a standard procedure, this ethynyl silane is lithiated with n-butyllithium then reacted with commercial flavanthrone to yield the diol intermediate 5, which is reductive-aromatized under acidic conditions to afford 6.

Sources & evidence

ORD record
ord-4bde73c44405481f85bac9469d40be6b
Source dataset
uspto-grants-2016_06
Patent number
US09373801B2

Reaction notes

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