Tetrahydrofuran → HCID 86606707, compound

HRID 2253425Notes

Reaction equation

HRID 2253425 reaction equation
[CH3:1][CH:2]([Si:4]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[O:5]C/C(/C)=C/C(OCC)=O)[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[CH3:17][CH:15]([Si:4]([CH:18]([CH3:20])[CH3:19])([CH:2]([CH3:3])[CH3:1])[O:5]/[C:27](/[CH3:31])=[CH:28]/[CH2:29][OH:30])[CH3:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86606705HCID 86606705, compound

Product 1

HCID 86606707HCID 86606707, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. solution of (E)-ethyl 4-[tris-(1-methylethyl)silyloxy]-3-methylbut-2-enoate (5 g, 17.6 mmol) in dry Et2O was added a solution of lithium aluminum hydride (17.6 mL, 17.6 mmol, 1 M in Et2O). After 30 minutes, the reaction mixture was neutralized by dropwise addition of THF followed by addition of a saturated solution of potassium sodium tartrate. The reaction mixture was stirred overnight and then diluted with Et2O. The organic layer was separated and washed with water, dried over MgSO4 and concentrated in vacuo to afford (E)-3-[tris-(1-methylethyl)silyloxy]but-2-en-1-ol as a colorless oil which was used directly into the next reaction.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4dbcafbd1014e71af28becfa0ebb6a2
Source dataset
uspto-grants-2008_01
Patent number
US07323604B2

Reaction notes

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