Tetrahydrofuran → HCID 21543865, compound

HRID 1606574Notes

Reaction equation

HRID 1606574 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]1([CH:18]2[CH2:24][C:23](=O)[NH:22][C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[S:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:12]1([CH:18]2[CH2:24][CH2:23][NH:22][C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[S:19]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 38949029476-22-0HCID 21226445Aluminium lithium hydride

Product 1

HCID 21543865HCID 21543865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A slurry of 24 g. of lithium aluminum hydride in 950 ml. of dry tetrahydrofuran is treated portionwise with 140 g. of finely-divided 2,3-dihydro-2-phenyl-1,5-benzothiazepin-4-one. The reaction is exothermic and the mixture is allowed to reflux during the addition. After stirring for 2 hours at room temperature, the mixture is refluxed for 3 hours, cooled and treated dropwise with 30 ml. of water and then a solution of 16 g. of sodium hydroxide in 100 ml. of water. The organic phase is filtered from the inorganic salt, washed with ether and the filtrate dried over magnesium sulfate. After evaporation of the solvent, the residue is fractionated to give 118.5 g. of liquid, b.p. 179°-181° (0.2 mm). The distillate slowly crystallized to a yellow solid, m.p. 62°-64°. A sample crystallized from isopropyl ether gave a granular colorless product, m.p. 65°-67°.

Workup

  1. temperatureto reflux during the addition
  2. temperaturethe mixture is refluxed for 3 hours
  3. temperaturecooled
  4. additiontreated dropwise with 30 ml
  5. filtrationThe organic phase is filtered from the inorganic salt
  6. washwashed with ether
  7. dry with materialthe filtrate dried over magnesium sulfate
  8. customAfter evaporation of the solvent
  9. customto give 118.5 g
  10. customThe distillate slowly crystallized to a yellow solid, m.p. 62°-64°
  11. customA sample crystallized from isopropyl ether
  12. customgave a granular colorless product, m.p. 65°-67°

Sources & evidence

ORD record
ord-105363657662441eaa228f5fd16d38af
Source dataset
uspto-grants-1976_04
Patent number
US03953469

Reaction notes

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