Sodium borohydride → HCID 71089357, compound

HRID 1410314Notes

Reaction equation

HRID 1410314 reaction equation
[CH2:1]([C:7]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:19]2[CH:18]=[C:17]3[C:20](=[O:24])[CH:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Na+]>C1COCC1.C(O)C>[CH2:25]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]3[CH:20]([OH:24])[CH:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 71089296HCID 71089296, compound

Product 1

HCID 71089357HCID 71089357, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 1000 mL round flask, 9,9-dihexyl-2-methyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (85 g, 211.1 mmol) was dissolved in THF 400 mL and ethanol 400 mL, and then stirred. Sodium borohydride (NaBH4) (10 g, 265.0 mmol) was added to the reaction product 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 and drying, to thereby obtain 82.0 g of 9,9-dihexyl-2-methyl-1,2,3,9-tetrahydrocyclopenta[b]fluoren-1-ol (yield: 96.0%) (two isomers), as highly viscous oil.

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. customdrying

Sources & evidence

ORD record
ord-4c521ba02c104106802e97265cf2424c
Source dataset
uspto-grants-2014_12
Patent number
US08921499B2

Reaction notes

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