HCID 19389990, compound → HCID 19390052, compound

HRID 1757225Notes

Reaction equation

HRID 1757225 reaction equation
C([Li])CCC.O.Cl.[Cl-].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1.[Si:35]([O:42][CH:43]1[CH2:55][CH2:54][C:46]2([CH2:51][CH2:50][CH:49]([CH:52]=O)[CH2:48][CH2:47]2)[CH2:45][CH2:44]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>O1CCCC1>[Si:35]([O:42][CH:43]1[CH2:55][CH2:54][C:46]2([CH2:47][CH2:48][CH:49](/[CH:52]=[CH:15]/[C:11]3[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=3)[CH2:50][CH2:51]2)[CH2:45][CH2:44]1)([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:37])[CH3:36].[Si:35]([O:42][CH:43]1[CH2:55][CH2:54][C:46]2([CH2:47][CH2:48][CH:49](/[CH:52]=[CH:15]\[C:11]3[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=3)[CH2:50][CH2:51]2)[CH2:45][CH2:44]1)([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 19389990HCID 19389990, compoundHCID 53659697HCID 53659697, compoundHCID 178418339Butyllithium

Product 2

HCID 19390052HCID 19390052, compoundHCID 70060377HCID 70060377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (0.92 ml; 1.6M solution in hexane) was added to a suspension of 0.217 g of (3-picolyl)triphenylphosphonium chloride hydrochloride monohydrate (Baker B. R. et al. J. Med. Chem. 1971, 14, 797) in 5 ml of anhydrous tetrahydrofuran, at 0° C. under nitrogen atmosphere. The yellow-orange mixture was stirred at room temperature for 0.5 hrs, then a solution of 0.05 g of 9-tert-butyldimethylsilyloxy-3-formyl-spiro[5.5]undecane (V, Prep. 8) in 1 ml of anhydrous tetrahydrofuran was added and the mixture was stirred at room temperature overnight. The reaction was quenched with a saturated aqueous solution of ammonium chloride. The layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The crude residue was purified by flash chromatography (SiO2 ; n-hexane/diethylether 70/30) to give 0.020 g of (E)-9-tert-butyldimethylsilyloxy-3-(2-(3-pyridyl)vinyl)-spiro[5.5]undecane and 0.020 g of (Z)-9-tert-butyldimethylsilyloxy-3-(2 -(3-pyridyl)vinyl)-spiro[5.5]undecane as white amorphous solids.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (SiO2 ; n-hexane/diethylether 70/30)

Sources & evidence

ORD record
ord-1a1a78641b9e41b683297cd790087a8d
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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