Sodium borohydride → 2-Methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluorene

HRID 2273383Notes

Reaction equation

HRID 2273383 reaction equation
[CH3:1][CH:2]1[C:45](=O)[C:5]2=[CH:6][C:7]3[C:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:9]4[C:14]([C:15]=3[CH:16]=[C:4]2[CH2:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=4.[BH4-].[Na+]>C1COCC1.C(O)C>[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([CH:45]=1)=[CH:6][C:7]1[C:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:9]3[C:14]([C:15]=1[CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 71089295HCID 71089295, compound

Product 1

HCID 866947952-Methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluoreneYield 78.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL round flask, 2-methyl-9,9-ditetradecyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (20 g, 31.9 mmol) was dissolved in 150 mL of THF and 150 mL of ethanol, and then stirred. Sodium borohydride (NaBH4) (1.8 g, 47.8 mmol) was added to the reactant in five lots, and then stirred for 12 hours. The resultant mixture, after removal of solvent, was dissolved in ethylacetate, and then washed with water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials. The dried reactant was dissolved in 150 mL of toluene, and then inputted to a round flask. After that, p-toluene sulfonic acid (0.08 g) was inputted thereto, and then water was completely removed under reflux with Dean-Stark. The resultant material was cooled to room temperature, and then an aqueous ammonium chloride solution (100 mL) and 200 mL of diethyl ether were injected thereto, followed by separation of the organic layer. The organic layer collected by extracting the residue with diethyl ether was dried over magnesium sulfate, followed by removal of volatile materials, and then purified by using silica gel column chromatography, to thereby obtain 15.3 g of 2-methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluorene (yield: 78.5%).

Workup

  1. customThe resultant mixture, after removal of solvent
  2. dissolutionwas dissolved in ethylacetate
  3. washwashed with water three times
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customfollowed by removal of volatile materials
  6. dissolutionThe dried reactant was dissolved in 150 mL of toluene
  7. custominputted to a round flask
  8. customwater was completely removed
  9. temperatureunder reflux with Dean-Stark
  10. customfollowed by separation of the organic layer
  11. customThe organic layer collected
  12. extractionby extracting the residue with diethyl ether
  13. dry with materialwas dried over magnesium sulfate
  14. customfollowed by removal of volatile materials
  15. custompurified

Sources & evidence

ORD record
ord-ee4f37052741489a962aa29becf1b1f4
Source dataset
uspto-grants-2015_09
Patent number
US09120884B2

Reaction notes

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