Water → HCID 20203616, compound

HRID 978785Notes

Reaction equation

HRID 978785 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13393783HCID 13393783, compound

Product 1

HCID 20203616HCID 20203616, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 16 g 4-chloro-3-formyl-flav-3-ene in 500 ml dry methanol at room temperature is added 0.5 g sodium borohydride in small portions. After the addition is completed 500 ml water is added. The solution is filtered and extracted with chloroform. The combined organic extracts are dried over magnesium sulfate and evaporated. Chromatographically pure 4-chloro-3-hydroxymethyl-flav-3-ene is obtained as a yellowish oil; TLC (SiO2, CHCl3): 1 spot, RF 0.18.

Workup

  1. additionAfter the addition
  2. additionis added
  3. filtrationThe solution is filtered
  4. extractionextracted with chloroform
  5. dry with materialThe combined organic extracts are dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e87b5e3c526641768db7b3c99aef5afb
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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