Ethyl chloroformate → HCID 22726773, compound

HRID 2085978Notes

Reaction equation

HRID 2085978 reaction equation
[C:1]([S:5][C:6]1[C:7]([C:12](O)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[BH4-].[Li+].[OH-].[Na+]>O1CCCC1.O.C(OCC)(=O)C.CO>[C:1]([S:5][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 118307273-TERT-BUTYLTHIO-2-CARBOXYPYRIDINE

Product 1

HCID 22726773HCID 22726773, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

To a suspension of 3-t-butylthio-2-carboxypyridine (10.0 g, 47.4 mmol) in tetrahydrofuran (200 mL) cooled to −5° C. was added trethylamine (8.25 mL, 47.4 mmol) followed by addition of ethyl chloroformate (4.38 g, 47.4 mmol) and reaction was stirred for 30 min at 0° C. Lithium borohydride (2.58 g, 118 mmol) was added in portions, maintaining the temperature below 5° C. After the addition was complete the reaction was allowed to warm to room temperature and stirred for 1 hour. Temperature was lowered to −5° C. and methanol (10 mL) was added followed by addition of aqueous sodium hydroxide (10 mL, 10%). After addition of ethyl acetate (50 mL) and water (40 mL) dilute hydrochloric acid was added to pH=5.0.

Workup

  1. additionwas added trethylamine (8.25 mL, 47.4 mmol)
  2. temperaturemaintaining the temperature below 5° C
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. stirringstirred for 1 hour
  6. customwas lowered to −5° C.
  7. additionwas added to pH=5.0

Sources & evidence

ORD record
ord-fa4526f156c44bcfa1e91beefc544788
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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