Hydrochloric Acid → HCID 59516008, compound

HRID 1160426Notes

Reaction equation

HRID 1160426 reaction equation
[BH4-].[Na+].[Cl-].[Li+].C[O:6][C:7](=O)[CH:8]=[CH:9][C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([CH:23]=[CH:24][C:25](OC)=[O:26])=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1.Cl>C(O)C.COCCOCCOC>[OH:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:20]([C:19]3[CH:18]=[CH:17][C:16]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:15][C:14]=3[CH2:13]2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 68680027HCID 68680027, compound

Product 1

HCID 59516008HCID 59516008, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8150DiglymeSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of sodium borohydride (3.7 g, 98 mmol) and lithium chloride (4.2 g, 101 mmol) in ethanol (70 ml) was stirred at 5° C. for 15 min, 9H-fluorene-2,7-diacrylic acid dimethyl ester (5.0 g, 15 mmol) in diglyme (150 ml) was added portionwise at 20-50° C. and the mixture was refluxed for 18 h. Diluted hydrochloric acid was added dropwise after cooling and the mixture was extracted with diethyl ether. Organic layer was separated, dried (MgSO4) and evaporated to give a residue, which was purified by chromatography on silica gel. Elution with ethyl acetate afforded 1.85 g (44%) of the title compound as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 18 h
  2. temperatureafter cooling
  3. extractionthe mixture was extracted with diethyl ether
  4. customOrganic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a residue, which
  8. customwas purified by chromatography on silica gel
  9. washElution with ethyl acetate

Sources & evidence

ORD record
ord-aa5a105edcc747da9d0cfa7c6baf6e3f
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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