Pentane → HCID 67043662, compound

HRID 473013Notes

Reaction equation

HRID 473013 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].[Li]C(C)(C)C.CCCCC.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C:21]1([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]1)[C:20]2=[N:33][S:34]([CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])(=[O:36])=[O:35].C(OC=C[Li])C>C1COCC1>[Br:16][C:17]1[CH:18]=[C:19]2[C:23]([CH2:22][C:21]3([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)[C:20]2([NH:33][S:34]([CH2:37][CH2:38][Si:39]([CH3:41])([CH3:40])[CH3:42])(=[O:36])=[O:35])[C:1]([O:3][CH2:4][CH3:5])=[CH2:2])=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 8003PentaneHCID 8023Ethyl vinyl etherHCID 67043529N-(5'-bromo-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-(trimethylsilyl)ethanesulfonamideHCID 178418306HCID 178418306, compoundHCID 178506908HCID 178506908, compound

Product 1

HCID 67043662HCID 67043662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl vinyl ether (7 mL, 73 mmol) in THF (10 mL) was added dropwise a solution of 1.7 M t-BuLi in pentane (26 mL, 44 mmol) at −78° C. under nitrogen. After 10 min, the reaction mixture was cooled in an ice bath and stirred for 45 min. To a solution of N-(5′-bromo-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-(trimethylsilyl)ethanesulfonamide (2) (1.3508 g, 2.86 mmol) in THF (20 mL) was added a solution of -ethoxyvinyllithium, obtained as described above, at −78° C. under nitrogen via a cannula. After 2 h, LC-MS indicated the disappearance of starting material. The reaction mixture was quenched with saturated NaHCO3 (5 mL) and saturated brine (20 mL) and then vigorously stirred at room temperature for 1 h. The mixture was extracted three times with EtOAc. The combined organic layers were dried over Na2SO4, filtered and evaporated. The crude product 9 (1.7654 g) was directly used in the next step without further purification. LC-MS tR=2.43 min in 3 min chromatography, m/z 544, 546 (MH+), 480, 482.

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. customobtained
  3. customat −78° C.
  4. waitAfter 2 h
  5. customThe reaction mixture was quenched with saturated NaHCO3 (5 mL) and saturated brine (20 mL)
  6. stirringvigorously stirred at room temperature for 1 h
  7. extractionThe mixture was extracted three times with EtOAc
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product 9 (1.7654 g) was directly used in the next step without further purification
  12. waitLC-MS tR=2.43 min in 3 min chromatography, m/z 544, 546 (MH+), 480, 482

Sources & evidence

ORD record
ord-09eeb51eab1e47ed8371aec7b53cfe91
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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