Sodium borohydride → HCID 231416, compound

HRID 1836895Notes

Reaction equation

HRID 1836895 reaction equation
C1(C)CCC(C(C)C)[CH:3]([C:10]2([CH:51]3C(C(C)C)CCC(C)C3)[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:20]4C(C(C)C)CCC(C)C4)[CH:18]=3)[C:13]([CH:40]3C(C(C)C)CCC(C)C3)([CH:30]3C(C(C)C)CCC(C)C3)[CH2:12][C:11]2=[O:50])C1.[BH4-].[Na+]>C(O)C>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:40])([CH3:30])[CH2:12][CH:11]([OH:50])[C:10]([CH3:3])([CH3:51])[C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23498909HCID 23498909, compound

Product 1

HCID 231416HCID 231416, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10 g (46.2 mmol) of 1,1,4,4,7-pentamenthyl-2-tetralone in 100 mL of ethyl alcohol was added 7 g (185 mmol) of sodium borohydride portionwise over 15 minutes. After the addition was complete the reaction was stirred at room temperature. After 16 hours the reaction mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with 5-10% ethyl acetate/hexane), followed by crystallization from hexane to afford 4 g (40%) of 3-methyl-6-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene.(M+=218).

Workup

  1. additionAfter the addition
  2. concentrationAfter 16 hours the reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (gradient elution with 5-10% ethyl acetate/hexane)
  8. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-ba57607b43c846c58e05df7914ac8698
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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