Water → HCID 58692104, compound

HRID 269453Notes

Reaction equation

HRID 269453 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]2.[Li][CH2:15][CH2:16][CH2:17][CH3:18].Cl[Si:20](Cl)([CH3:22])[CH3:21].O>CCOCC>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH:6]2[Si:20]([CH:15]1[C:6]2[C:18](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[CH:17]=[C:16]1[CH:8]([CH3:9])[CH3:7])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6398DichlorodimethylsilaneHCID 69277189HCID 69277189, compoundHCID 178418339Butyllithium

Product 1

HCID 58692104HCID 58692104, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 23.7 g (100 mmol) of 4-bromo-2-isopropyl-1H-indene in 600 ml of ether, 40.0 ml (100 mmol) of 2.5 M nBuLi in hexanes was added at room temperature. The mixture was stirred for 24 h at this temperature, and then 6.45 g (50.0 mmol) of dichlorodimethylsilane was added. The resulting mixture was stirred for 36 h at ambient temperature, and then 200 ml of water was added. The organic layer was separated, dried over Na2SO4, and evaporated to dryness. The product was isolated by MPLC on Silica Gel 60 (40-63 um, d 50 mm, l 500 mm; eluent—hexanes). Yield 16.6 g (63%) of a ca. 4:3 mixture of rac- and meso-products.

Workup

  1. stirringThe resulting mixture was stirred for 36 h at ambient temperature
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe product was isolated by MPLC on Silica Gel 60 (40-63 um, d 50 mm, l 500 mm; eluent—hexanes)
  6. additionYield 16.6 g (63%) of a ca. 4:3 mixture of rac- and meso-products

Sources & evidence

ORD record
ord-a4d043f57eaf464b90117180cafe87f2
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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