Tetrahydrofuran → HCID 58380155, compound

HRID 404344Notes

Reaction equation

HRID 404344 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([C:12](OCCC)=[O:13])[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)[CH2:2][CH2:3][CH3:4].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 67360855HCID 67360855, compound

Product 1

HCID 58380155HCID 58380155, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of T13.1 (795 mg, 2230 μmol) and THF (10 mL) at 0° C. was added LAH (1.0 M solution in THF (3345 μL, 3345 μmol)). The reaction was stirred for one hour and then carefully diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and then dried over sodium sulfate, filtered, and concentrated to provide T13.2 (530 mg, 83.0% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide T13.2 (530 mg, 83.0% yield)

Sources & evidence

ORD record
ord-aa1441a2612749c59f80d7bd40bd4af9
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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