Sodium borohydride → HCID 20542033, compound

HRID 2286184Notes

Reaction equation

HRID 2286184 reaction equation
[CH2:1]1[O:20][CH:4]([CH:5]2[CH2:14][CH2:13][C:12]3[C:7](=[C:8]([O:17][CH3:18])[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=3)[C:6]2=[O:19])[O:3][CH2:2]1.OC=C1CCC2C(=C(OC)C=C(OC)C=2)C1=O.[BH4-].[Na+]>CC(O)C>[CH2:2]1[O:3][CH:4]([CH:5]2[CH2:14][CH2:13][C:12]3[C:7](=[C:8]([O:17][CH3:18])[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=3)[CH:6]2[OH:19])[O:20][CH2:1]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 20542010HCID 20542010, compoundHCID 70553603HCID 70553603, compound

Product 1

HCID 20542033HCID 20542033, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of crude 1,2,3,4-tetrahydro-6,8-dimethoxy-1-oxo-2-naphthaldehyde ethylene acetal obtained from 5.73 g. of 2-hydroxymethylene-6,8-dimethoxy-1-tetralone, and 0.91 g. of sodium borohydride in 25 ml. of 2-propanol was stirred two hours at room temperature. The mixture was cooled and treated with 80 ml. of saturated aqueous ammonium chloride and extracted with ether. The ethereal extracts were washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride, dried over anhydrous magnesium sulfate and evaporated to dryness to give 1,2,3,4-tetrahydro-1-hydroxy-6,8-dimethoxy-2-naphthaldehyde ethylene acetal which was converted directly to 3,4-dihydro-6,8-dimethoxy-2-naphthaldehyde as described hereinabove in Example 154.

Workup

  1. customobtained from 5.73 g
  2. temperatureThe mixture was cooled
  3. additiontreated with 80 ml
  4. extractionof saturated aqueous ammonium chloride and extracted with ether
  5. washThe ethereal extracts were washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-618eb7d2d60449e5a6aa742cd0281787
Source dataset
uspto-grants-1982_04
Patent number
US04327022

Reaction notes

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