1H-Indene, 2-methyl- → HCID 137327313, compound

HRID 1293579Notes

Reaction equation

HRID 1293579 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Li+].CCC[CH2-].[Cl-].[CH3:17][SiH:18]([C:20]1[C:27]2[C:23]([CH:24]=[CH:25][CH:26]=2)=[CH:22][C:21]=1[S:28][CH3:29])[CH3:19]>C1COCC1.CCCCCC>[CH3:19][SiH:18]([C:20]1[C:21]([S:28][CH3:29])=[C:22]([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])[C:23]2[C:27]=1[CH:26]=[CH:25][CH:24]=2)[CH3:17]

Participants

6

Reactant 3

HCID 165871H-Indene, 2-methyl-HCID 61028n-Butyl lithiumHCID 178503319HCID 178503319, compound

Product 1

HCID 137327313HCID 137327313, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a 250 mL round bottom flask with sidearm, stirring bar, and 60 mL dropping funnel was added 2-methylindene (13 g, 100 mmol, product made by Boulder) dissolved in THF (20 mL). N-Butyllithium (100 mmol, 40 mL of a 1.6 M solution in hexane) was added dropwise at room temperature. After addition was complete, the flask and contents were stirred an additional 2 h. A solution containing dimethylsilyl(2-methylthiopentalene)chloride in THF (30 mL) was added dropwise at room temperature. Stirring was continued for 1 hour, after which time the reaction was quenched with 30 mL of a 30% water/THF mixture, concentrated on a rotary evaporated, and a sample submitted for analysis.

Workup

  1. additionAfter addition
  2. stirringthe flask and contents were stirred an additional 2 h
  3. additionwas added dropwise at room temperature
  4. stirringStirring
  5. customafter which time the reaction was quenched with 30 mL of a 30% water/THF mixture
  6. concentrationconcentrated on a rotary evaporated

Sources & evidence

ORD record
ord-814a585d37c04dde839fccca9f3125f5
Source dataset
uspto-grants-2007_07
Patent number
US07238818B2

Reaction notes

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