chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilane → [4-(4-t-butylphenyl)-2-isopropyl-1H-inden-1-yl][4-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-1-yl]dimethylsilane

HRID 271799Notes

Reaction equation

HRID 271799 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[C:13]3[CH:21]=[C:22]([CH3:24])[CH2:23][C:12]=23)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.C([Cu])#N.Cl[Si:34]([CH:37]1[C:45]2[C:40](=[C:41]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:48][CH:47]=3)[CH:42]=[CH:43][CH:44]=2)[CH:39]=[C:38]1[CH:56]([CH3:58])[CH3:57])([CH3:36])[CH3:35]>CCOCC.CCCCCC.O>[C:52]([C:49]1[CH:50]=[CH:51][C:46]([C:41]2[CH:42]=[CH:43][CH:44]=[C:45]3[C:40]=2[CH:39]=[C:38]([CH:56]([CH3:58])[CH3:57])[CH:37]3[Si:34]([CH:21]2[C:13]3=[CH:14][C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=4[C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=4)=[C:12]3[CH:23]=[C:22]2[CH3:24])([CH3:36])[CH3:35])=[CH:47][CH:48]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

8

Reactant 4

HCID 21880365chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilaneHCID 866134919-(4-tert-Butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthaleneHCID 178418339ButyllithiumHCID 178418546HCID 178418546, compound

Product 1

HCID 68747072[4-(4-t-butylphenyl)-2-isopropyl-1H-inden-1-yl][4-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-1-yl]dimethylsilane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Solution of 9-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalene (4d, 2.97 g, 9.38 mmol) in Et2O (50 ml) was cooled to −60° C., and n-BuLi (1.6 M in hexane, 6.04 ml, 9.67 mmol) was added. The resulting mixture was allowed to warm to room temperature, stirred for 3 h, cooled to −60° C., and CuCN (50 mg, 0.55 mmol) was added. After 15 min, solution of chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilane (9.67 mmol) in Et2O (24 ml) was added, and resulting mixture was allowed to warm to room temperature and stirred for 16 h. Water (5 ml) and hexane (200 ml) were added, organic phase was separated, dried over MgSO4, passed through silica gel and evaporated. The product was dried in vacuo and used without purification.

Workup

  1. temperaturecooled to −60° C.
  2. waitAfter 15 min
  3. customresulting mixture
  4. temperatureto warm to room temperature
  5. stirringstirred for 16 h
  6. customorganic phase was separated
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe product was dried in vacuo
  10. customused without purification

Sources & evidence

ORD record
ord-29e121320f7f4e1b8f03331188a2c47d
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

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