Methyl 3-(5-trimethylsilyl-3-furyl)propionate → 3-(2-Trimethylsilyl-4-furyl)propan-1-ol

HRID 488219Notes

Reaction equation

HRID 488219 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]1[O:4][CH:5]=[C:6]([CH2:8][CH2:9][C:10](OC)=[O:11])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:15][Si:2]([CH3:1])([CH3:14])[C:3]1[O:4][CH:5]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[CH:7]=1

Participants

4

Reactant 2

HCID 19019871Methyl 3-(5-trimethylsilyl-3-furyl)propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 150370913-(2-Trimethylsilyl-4-furyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 3-(2-trimethylsilyl-4-furyl)-propionate (from above) in tetrahydrofuran (3 ml) was added dropwise to a suspension of lithium aluminum hydride (27 mg) in tetrahydrofuran (4 ml) at room temperature. After 3 hours, the mixture was quenched with ethyl acetate and extracted with ether. Evaporation of the dried (magnesium sulphate) extracts gave the title alcohol, which was used in the next step without purification.

Workup

  1. customthe mixture was quenched with ethyl acetate
  2. extractionextracted with ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulphate)

Sources & evidence

ORD record
ord-cdd5543b6bb544db9eab788aeaf48049
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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