Tetrahydrofuran → HCID 117817947, compound

HRID 1772399Notes

Reaction equation

HRID 1772399 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH:20]([CH3:27])[C:21]3=[O:26])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].C1COCC1>C(O)C>[C:13]([C:11]1[CH:10]=[C:9]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH:20]([CH3:27])[CH:21]3[OH:26])[CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 22173462HCID 22173462, compound

Product 1

HCID 117817947HCID 117817947, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.35 g, 61.98 mmol, 1.5 equiv) was added in portions to a cold solution (0° C.) of compound 9 (13.8 g, 41.32 mmol, 1.0 equiv), THF (140 mL) and ethanol (140 mL). The reaction mixture was stirred at room temperature for 2 hours when LC/MS indicated that the reaction was complete. The mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (300 mL). 1M HCL was added dropwise to quench the reaction. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated brine (500 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude compound 10 (15 g, >99% yield) as a pale-yellow oil. This material was used subsequently.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (300 mL)
  3. addition1M HCL was added dropwise
  4. customto quench
  5. customthe reaction
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  8. washThe combined organic layers were washed with saturated brine (500 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ba6b879e0c84ce0a5cd1a6b35ad2125
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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