Hydrochloric Acid → HCID 21408132, compound

HRID 840024Notes

Reaction equation

HRID 840024 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1.Cl>CO>[F:3][C:4]1[CH:13]=[C:12]2[C:7](=[CH:6][CH:5]=1)[CH2:8][CH:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH:11]2[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20335104HCID 20335104, compound

Product 1

HCID 21408132HCID 21408132, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 8 g. of sodium borohydride and 150 ml. of methanol, 23.5 g. of 7-fluoro-3-(methoxycarbonylmethyl)-1-tetralone are added. The mixture is diluted with 250 ml. of 2N hydrochloric acid after standing for four hours at 25° C; the aqueous mixture is then extracted with chloroform. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, and evaporated to yield methyl 6-fluoro-4-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate. The latter compound is dehydrogenated by the process described in Part B of Example 2 to furnish methyl 6-fluoro-4-hydroxy-2-naphthylacetate.

Workup

  1. additionTo a mixture of 8 g
  2. additionThe mixture is diluted with 250 ml
  3. extractionthe aqueous mixture is then extracted with chloroform
  4. washwashed with water to neutrality
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-02f4786ff7884cb0874c07021aebe129
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

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