Hydrochloric Acid → HCID 21408132, compound

HRID 1973979Notes

Reaction equation

HRID 1973979 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-abbf92843c66475da643cb915e4db7e1
Source dataset
uspto-grants-1976_12
Patent number
US03998966

Reaction notes

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