Diethyl Ether → HCID 20389861, compound

HRID 426775Notes

Reaction equation

HRID 426775 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:22][C:21]3[S:23][CH:24]=[CH:25][C:20]=3[C:19]([C:26](O)=[O:27])=[CH:18][C:17]=2[CH:29]=1.O1CCCC1>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:22][C:21]3[S:23][CH:24]=[CH:25][C:20]=3[C:19]([CH2:26][OH:27])=[CH:18][C:17]=2[CH:29]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8028TetrahydrofuranHCID 20389862HCID 20389862, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20389861HCID 20389861, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40 ml of abs. ether is added at 3° under nitrogen 0.76 g (0.02 mole) of lithium aluminium hydride, and there is then added dropwise at 5° with stirring, in the course of half an hour, a solution of 2.9 g (0.01 mole) of 7-chlorobenzo[f]thieno [2,3-b]thiepin-4-carboxylic acid in 60 ml of abs. ether and 20 ml of abs. tetrahydrofuran. The mixture is subsequently stirred for 2 hours at room temperature; 4 ml of water is then slowly added dropwise at 5°, and the precipitate is filtered off with suction. The filtrate is concentrated in vacuo; the crude residue is chromatographed on a silica-gel column, and by elution with chloroform is yielded 7-chlorobenzo[f]thieno [2,3-b]thiepin-4-methanol, m.p. 117°-120°.

Workup

  1. additionis then added dropwise at 5°
  2. stirringThe mixture is subsequently stirred for 2 hours at room temperature
  3. filtrationthe precipitate is filtered off with suction
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe crude residue is chromatographed on a silica-gel column
  6. washby elution with chloroform

Sources & evidence

ORD record
ord-7c50553e80e2468585a9b96b5fd1fd9d
Source dataset
uspto-grants-1979_10
Patent number
US04171366

Reaction notes

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