Tetrahydrofuran → HCID 18787417, compound

HRID 342081Notes

Reaction equation

HRID 342081 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH:4](C(OCC)=O)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:26][CH2:25]C1>>[O:1]1[C:7]2=[CH:8][CH:9]=[CH:10][C:11]([CH2:25][OH:26])=[C:6]2[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 18787431HCID 18787431, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18787417HCID 18787417, compound

Procedure

A solution of ethyl 2,3,4,5-tetrahydrobenzoxepin-4-carboxylate (2.85 g, 13 mmol) in THF (30 ml) was stirred as LAH (1 g, 26 mmol) was slowly added. The mixture was stirred for 18 hr, and then quenched by the sequential addition of water (1 ml), 15% sodium hydroxide (1 ml), and water (3 ml). The mixture was filtered and the filter cake washed with ethanol. The filtrate was concentrated in vacuo to an oil (2.3 g, 100%).

Workup

  1. additionwas slowly added
  2. customquenched by the sequential addition of water (1 ml), 15% sodium hydroxide (1 ml), and water (3 ml)
  3. filtrationThe mixture was filtered
  4. washthe filter cake washed with ethanol
  5. concentrationThe filtrate was concentrated in vacuo to an oil (2.3 g, 100%)

Sources & evidence

ORD record
ord-354daf5979ca4ded8188822fa4493a6a
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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