Water → (3-Chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)methanol

HRID 1004114Notes

Reaction equation

HRID 1004114 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 28528713-Chloro-5,6-dimethoxy-1-benzothiophene-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10956261(3-Chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 68 mmol of the compound obtained in Step B in 150 ml of tetrahydrofuran is added at 5° C. under an inert atmosphere to a solution of 0.1 mol of LiAlH4 in 60 ml of tetrahydrofuran. After 4 hours' reaction at room temperature, the reaction mixture is hydrolysed by the addition of water and then by an aqueous 2N sodium hydroxide solution. After 12 hours at room temperature, the reaction mixture is filtered over Celite. The organic phase is then concentrated under reduced pressure, taken up in dichloromethane and washed with water and then with a saturated NaCl solution. After the organic phase has been dried over calcium sulphate, the solution is concentrated under reduced pressure, enabling 15.7 g of the expected product to be obtained.

Workup

  1. customAfter 4 hours' reaction at room temperature
  2. filtrationthe reaction mixture is filtered over Celite
  3. concentrationThe organic phase is then concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialAfter the organic phase has been dried over calcium sulphate
  6. concentrationthe solution is concentrated under reduced pressure
  7. customto be obtained

Sources & evidence

ORD record
ord-d5980ec00f1c4e099938d0d7e4de1826
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Reaction notes

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