Water → HCID 23436675, compound

HRID 992789Notes

Reaction equation

HRID 992789 reaction equation
[Na].[CH:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.[CH3:7][C:8]1([CH3:17])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10](=O)[CH2:9]1.O.[CH2:19](OCC)C>>[CH3:7][C:8]1([CH3:17])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH:10]([C:3]2[C:2](=[CH2:19])[CH:6]=[CH:5][CH:4]=2)[CH2:9]1

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 7612CyclopentadieneHCID 843993,3,5,5-TetramethylcyclohexanoneHCID 5360545Sodium

Product 1

HCID 23436675HCID 23436675, compound

Procedure

Hexane washed sodium spheres (2.40 g, 104 mmol) were slowly added to 100 mL absolute ethanol. The sodium had fully reacted before cyclopentadiene (6.0 mL, 72.6 mmol) and 3,3,5,5-tetramethylcyclohexanone (10.0 mL, 57.1 mmol) were added. After 30 hours, the reaction was poured into 200 mL water and 100 mL diethyl ether were added. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (3×50 mL). The combined organic layers were extracted with water (3×50 mL), dried over MgSO4, filtered, and rotavapped to produce the product in quantitative yield as a yellow oil. MS (GC-MS) m/z 202.3 (M+). 1H NMR (CDCl3): δ 0.97 (s, 12H, CH3), 1.04.(s, 2H, CH2), 2.39 (s, 4H, CH2), 6.52, 6.52 (m, 4H, fulvene-H).

Workup

  1. washHexane washed sodium
  2. additionwere slowly added to 100 mL absolute ethanol
  3. additionwere added
  4. additionwere added
  5. customThe organic layer was isolated
  6. extractionthe aqueous layer was extracted with diethyl ether (3×50 mL)
  7. extractionThe combined organic layers were extracted with water (3×50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customto produce the product in quantitative yield as a yellow oil

Sources & evidence

ORD record
ord-1cff560bc503449f97e42d5e7701e9af
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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