Water → HCID 58972225, compound

HRID 922073Notes

Reaction equation

HRID 922073 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][C:20]#N.[BH4-].[Na+].O.CC([O:30]C)(C)C>CO>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][CH2:20][OH:30]

Participants

6

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 58972229HCID 58972229, compound

Product 1

HCID 58972225HCID 58972225, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude (E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enenitrile in MeOH (3 mL) was cooled to 0° C. and treated with NaBH4 (64.3 mg, 1.74 mmol), which gave immediate effervescence. After 12 h, H2O (10 mL) was added (caution: copious gas evolution), MTBE (10 mL) was added, separated and the aqueous phase extracted with MTBE (3×10 mL). The combined organics were washed with H2O (10 mL), brine (10 mL), dried over Na2SO4 and concentrated to give (E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-en-1-ol as a pale yellow oil.

Workup

  1. customgave immediate effervescence
  2. additionwas added
  3. customseparated
  4. extractionthe aqueous phase extracted with MTBE (3×10 mL)
  5. washThe combined organics were washed with H2O (10 mL), brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8d458c3d2ac645058e5be73f788059bf
Source dataset
uspto-grants-2016_03
Patent number
US09278085B2

Reaction notes

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