Sodium borohydride → HCID 53943144, compound

HRID 1638802Notes

Reaction equation

HRID 1638802 reaction equation
[CH3:1]OC1C(OC)=CC2C(=O)CCCCC=2C=1.C[O-].[Na+].[CH3:20][O:21][C:22]1[C:23]([O:37][CH3:38])=[CH:24][C:25]2[C:31](=[O:32])[CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:36]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:1][O:34][C:33]([CH:30]1[CH2:29][CH2:28][CH2:27][C:26]2[CH:36]=[C:22]([O:21][CH3:20])[C:23]([O:37][CH3:38])=[CH:24][C:25]=2[CH:31]1[OH:32])=[O:35]

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 10942334Sodium Methoxide2×HCID 12251715951-99-5HCID 19841227HCID 19841227, compound

Product 1

HCID 53943144HCID 53943144, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Using 2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (10 g), powdery sodium methoxide [prepared by subjecting a 28% methanol solution of sodium methoxide (40 g) to concentration to dryness under reduced pressure] and dimethyl carbonate (150 g), a condensation reaction is carried out in a manner as that described in Example 42. The resulting methyl ester of 2,3-dimethoxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid is dissolved in a mixture of methanol (100 ml) and methylene chloride (100 ml). The solution is subjected to reduction in a manner as that described in Example 42, using sodium borohydride (2 g). The product is purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1) to afford 2,3-dimethoxy-5-hydroxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid methyl ester (8 g) as a pale yellow oil.

Workup

  1. customprepared
  2. concentrationto concentration to dryness under reduced pressure] and dimethyl carbonate (150 g)
  3. customa condensation reaction
  4. customThe product is purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-9e178991704b4ac6a8839ff929a7ad6b
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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