HCID 12760710, compound → HCID 12760711, compound

HRID 1105986Notes

Reaction equation

HRID 1105986 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:18])[C:15](O)=[O:16])=[O:7]>O1CCCC1.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:18])[CH2:15][OH:16]

Participants

4

Reactant 1

HCID 12760710HCID 12760710, compound

Product 1

HCID 12760711HCID 12760711, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To 640 ml. of 1.0 M. boranetetrahydrofuran complex in tetrahydrofuran is added a solution of 81 g. of 8-(2-furoyl)-2-hydroxyoctanoic acid in 240 ml. of tetrahydrofuran during one hour while maintaining a temperature of 0°-10° C. After the addition, the solution is stirred at room temperature for 3 hours, is cooled to 0° C., and treated cautiously with 80 ml. of 1:1 aqueous tetrahydrofuran. The resulting mixture is diluted with ethyl acetate. The solution is washed successively with an ice-cold brine-hydrochloric acid mixture, brine, brinesodium bicarbondate solution and brine. The solution is dried over magnesium sulfate and concentrated to give an oil; pmr (CDCl3) δ 4.70 (triplet).

Workup

  1. additionAfter the addition
  2. temperatureis cooled to 0° C.
  3. additiontreated cautiously with 80 ml
  4. washThe solution is washed successively with an ice-cold brine-hydrochloric acid mixture, brine, brinesodium bicarbondate solution and brine
  5. dry with materialThe solution is dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil

Sources & evidence

ORD record
ord-d807e76ebc7d4887ada38e72f58a7977
Source dataset
uspto-grants-1982_01
Patent number
US04310700

Reaction notes

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