HCID 14802187, compound → HCID 14802188, compound

HRID 2308875Notes

Reaction equation

HRID 2308875 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[C:9]([CH3:28])=[C:10]([CH3:27])[C:11]2[O:15][CH:14]([CH2:16][CH2:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20](O)=[O:21])[S:13][C:12]=2[C:25]=1[CH3:26]>O1CCCC1>[OH:7][C:8]1[C:9]([CH3:28])=[C:10]([CH3:27])[C:11]2[O:15][CH:14]([CH2:16][CH2:17][CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20][OH:21])[S:13][C:12]=2[C:25]=1[CH3:26]

Participants

4

Reactant 2

HCID 14802187HCID 14802187, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14802188HCID 14802188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.3 g of lithium aluminum hydride was suspended in 30 ml of tetrahydrofuran, and a solution of 1.7 g of 5-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)-2,2-dimethylpentanoic acid (prepared as described in Example 81) in 5 ml of tetrahydrofuran was added dropwise under a stream of nitrogen and with ice-cooling to the suspension. After the dropwise addition, the reaction mixture was kept at room temperature for 1 hour and was then heated under reflux for 2 hours. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the ethyl acetate was distilled off under reduced pressure. The resulting residue was subjected to silica gel Lobar column chromatography, and the title compound was obtained by elution with a 9:1 by volume mixture of benzene and ethyl acetate.

Workup

  1. temperaturecooling to the suspension
  2. additionAfter the dropwise addition
  3. temperaturewas then heated
  4. temperatureunder reflux for 2 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationafter which the ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4ba877b6346f4503a4e7db003c50b65f
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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