77528-46-2 → 4,5,6,7-Tetrahydro-4-benzothiazolemethanol

HRID 1156956Notes

Reaction equation

HRID 1156956 reaction equation
C([O:3][C:4]([CH:6]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[CH2:9][CH2:8][CH2:7]1)=O)C>O1CCCC1>[OH:3][CH2:4][CH:6]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 1

HCID 1291773977528-46-2

Product 1

HCID 129177514,5,6,7-Tetrahydro-4-benzothiazolemethanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.14 g (30 mmoles) of AlLiH4 in 50 ml anhydrous tetrahydrofuran, cooled to -20° C. and maintained at that temperature, are slowly added 6.66 g (30 mmoles) of the above derivative (III) dissolved in 30 ml anhydrous THF. After 30 minutes at -20° C., excess AlLiH4 is destroyed by addition of isopropanol at -20° C. followed by 5 ml saturated aqueous sodium chloride, and is then stirred for 2 hrs. The resulting precipitate is filtered off and washed with ethyl acetate; the filtrate is evaporated and the oily residue is taken up in the hot with hexane; product (IV) crystallizes on cooling. Yield: 70%. M.p.=74°-75° C.

Workup

  1. temperaturemaintained at that temperature
  2. customexcess AlLiH4 is destroyed by addition of isopropanol at -20° C.
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with ethyl acetate
  5. customthe filtrate is evaporated
  6. customproduct (IV) crystallizes
  7. temperatureon cooling

Sources & evidence

ORD record
ord-576fccfef35a48de923dafb78e3dac26
Source dataset
uspto-grants-1982_06
Patent number
US04337343

Reaction notes

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