Dichlorodimethylsilane → Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

HRID 1922325Notes

Reaction equation

HRID 1922325 reaction equation
[CH3:1][CH:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[CH:4]=[C:3]1[CH3:10].CC1C2C=CSC=2CC=1C.[Li]CCCC.[Cl:26][Si:27](Cl)([CH3:29])[CH3:28]>C1COCC1>[Cl:26][Si:27]([CH:4]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:2]([CH3:1])=[C:3]1[CH3:10])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 123075884,5-dimethyl-4H-cyclopenta[b]thiopheneHCID 668093064,5-dimethyl-6H-cyclopenta[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, to a solution of 10.0 g (66.6 mmol) of a mixture of 4,5-dimethyl-4H-cyclopenta[b]thiophene and 4,5-dimethyl-6H-cyclopenta[b]thiophene in 150 ml of THF, 26.6 ml of 2.5 M (66.6 mmol) nBuLi in hexanes was added dropwise over 30 min at −60° C. This mixture was additionally stirred for 2 h at room temperature and then added dropwise over 3 h to a solution of 23.7 ml (25.2 g, 200 mmol) of dichlorodimethylsilane in 50 ml of THF. The resulting mixture was stirred for 12 h at ambient temperature and then evaporated to dryness. Fractional distillation gave a yellowish liquid, bp 83-85° C./0.2 mm Hg. Yield 10.7 g (66%).

Workup

  1. stirringThe resulting mixture was stirred for 12 h at ambient temperature
  2. customevaporated to dryness
  3. distillationFractional distillation
  4. customgave a yellowish liquid, bp 83-85° C./0.2 mm Hg

Sources & evidence

ORD record
ord-3039e99700e242b8b2b617f3b687cbd0
Source dataset
uspto-grants-2012_05
Patent number
US08173828B2

Reaction notes

Loading…