Ethyl Acetate → 6-(Hydroxymethyl)benzothiazole

HRID 1498957Notes

Reaction equation

HRID 1498957 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10](OCC)=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl.CCCCCC.O>[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 8857Ethyl Acetate2×HCID 516892Sodium BicarbonateHCID 10512520Ethyl benzo[d]thiazole-6-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178603856-(Hydroxymethyl)benzothiazoleYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Ethyl benzothiazole-6-carboxylate (2.10 g, 10.0 mmol) prepared in the Step 36-1-2 was dissolved in dichloromethane (80 ml), and under an ice cooling, a solution (1.5 mol/L) (20 ml, 30.0 mmol) of diisobutylaluminum hydride in hexane was slowly added thereto. The mixture was stirred at a room temperature for one hour, and then ethyl acetate (10 ml) and a saturated sodium bicarbonate solution were added to the mixture. Ethyl acetate and water were added thereto, the resulting mixture was subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (0.61 g, 37%) as a yellowish-brown oily substance.

Workup

  1. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9c69c1afe0f14a41a3cda91a630c0c54
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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