Diethyl Ether → HCID 14013850, compound

HRID 255443Notes

Reaction equation

HRID 255443 reaction equation
[H-].[Na+].[C:3]([SH:7])([CH3:6])([CH3:5])[CH3:4].[F:8][CH:9]([F:31])[C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12](Br)[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)C>C1COCC1>[C:3]([S:7][C:12]1[C:11]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:10]([CH:9]([F:31])[F:8])[N:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[C:13]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 14013849HCID 14013849, compound

Product 1

HCID 14013850HCID 14013850, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.44 g (0.011 mol) of 60of NaH in mineal oil dispersion was washed twice with 10 ml portions of dry THF. To the resulting oil free NaH was added 30 ml of dry THF followed by 1.08 g (1.4 ml, 0.012 mol) of t-butylmercaptan. The resulting mixture was heated up to 50° C. for 20 minutes and a white precipitate was formed. This suspension was added dropwise at room temperture to a solution of 4.20 g (0.01 mol) of product of Example 106 in 40 ml of dry THF. The reaction temperature rose to 35° C. After stirring at room temperature for 3 hours, the reaction mixture was poured into 3.7HCl. The aqueous layer was extractad twice with diethyl ether, dried (MgSO4) and concentrated to give 4.23 g of a light yellow oil. The crude product was purified by HPLC using 2EtOAC/cyclohexane as eluting solvent followed by kugelrohr distillation at 100°-110 ° C./100 Pa to give 2.86 g (67) of product as a colorless oil, nD25 1.4678.

Workup

  1. washwas washed twice with 10 ml portions of dry THF
  2. additionTo the resulting oil free NaH was added 30 ml of dry THF
  3. customa white precipitate was formed
  4. customrose to 35° C
  5. additionthe reaction mixture was poured into 3.7HCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92d8ab5c003b46eda5f2c42153506444
Source dataset
uspto-grants-1987_10
Patent number
US04698093

Reaction notes

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