Water → HCID 19027592, compound

HRID 864990Notes

Reaction equation

HRID 864990 reaction equation
[C:1]([O:20][CH2:21][CH:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C.C(O)C>[C:1]([O:20][CH2:21][CH:22]([CH2:27][CH2:26][OH:25])[CH2:23][OH:24])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 19027604HCID 19027604, compoundHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 19027592HCID 19027592, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

α-Trityloxymethyl-γ-butyrolactone (60.21 g, 0.168 mol) was added in small portions to a stirred suspension of lithium aluminium hydride (9.53 g, 0.251 mol) in dry tetrahydrofuran (300 ml) and the mixture was refluxed for 1 h. Slow addition of 10 ml H2O+10 ml 15% NaOH and 30 ml H2O produced a white sandy precipitation which was filtered off and washed with 2×50 ml tetrahydrofuran. The filtrate was evaporated to a small volume and dissolved in diethyl ether (300 ml), silica gel (250 g) was added and the mixture was carefully evaporated to a homogeneous powder. In a chromatography column the crude product--silica gel mixture was placed on top of silica gel (250 g) in n-hexane. Eluting with ethyl acetate+n-hexane (1+3), 2200 ml, removed trityl alcohol. Further eluting with ethyl acetate+ethanol (9+1) gave fractions 2900-3700 ml (from start), which after evaporation in vacuum produced a crystallizing oil. Yield 52.77 g (87%). TLC on silica: ethyl acetate+n-hexane (1+3), Rf 0.05; ethyl acetate+ethanol (9+1), Rf 0.81.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customproduced
  3. customa white sandy precipitation which
  4. filtrationwas filtered off
  5. washwashed with 2×50 ml tetrahydrofuran
  6. customThe filtrate was evaporated to a small volume
  7. dissolutiondissolved in diethyl ether (300 ml)
  8. additionsilica gel (250 g) was added
  9. customthe mixture was carefully evaporated to a homogeneous powder
  10. washEluting with ethyl acetate+n-hexane (1+3), 2200 ml
  11. customremoved trityl alcohol
  12. washFurther eluting with ethyl acetate+ethanol (9+1)
  13. customgave fractions 2900-3700 ml (from start), which
  14. customafter evaporation in vacuum
  15. customproduced a crystallizing oil

Sources & evidence

ORD record
ord-f26155c3e8d9470084f26cd2c0cb133f
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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