Tetrahydrofuran → HCID 18787417, compound

HRID 1107537Notes

Reaction equation

HRID 1107537 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-b6030e43f24341a2b182343398abc3f6
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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