Hydrochloric Acid → HCID 88223057, compound

HRID 2371487Notes

Reaction equation

HRID 2371487 reaction equation
N[CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)/[C:5](=[CH:13]\[C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=2)/[C:4]=1[CH3:22].Cl[O:24]C(C)(C)C.CC(C)([O-])C.[K+].Cl>CCOCC.C(O)C>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)/[C:5](=[CH:13]\[C:14]1[CH:15]=[CH:16][C:17]([S:20][CH3:21])=[CH:18][CH:19]=1)/[C:4]([CH3:22])=[C:3]2[CH:2]=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 521297Tert-Butyl hypochloriteHCID 23665647Potassium tert-butoxideHCID 70230538HCID 70230538, compound

Product 1

HCID 88223057HCID 88223057, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of freshly liberated amine from Step 1 (11.5 g, 37 mmol) in ether (220 mL) at 0° C. there was added a solution of t-butyl hypochlorite (4.0 g) in ether (10 mL); the mixture was stirred at 0° C. for 5 minutes as a yellow solid formed. The mixture was then allowed to warm up to room temperature and there was slowly added a solution of potassium tert-butoxide (15 g, 133 mmol) in ethanol (200 mL). The mixture was boiled on a steam bath for 10 minutes and then cooled down. There was added 1N aqueous HCl (200 mL) and after stirring for 20 minutes, the mixture was extracted with ether to afford the crude aldehyde which was purified by column chromatography on silica gel, eluting with a 1:5 mixture of ethyl acetate:hexane. The pure title compound was obtained as an oil.

Workup

  1. customformed
  2. temperatureto warm up to room temperature
  3. waitThe mixture was boiled on a steam bath for 10 minutes
  4. temperaturecooled down
  5. stirringafter stirring for 20 minutes
  6. extractionthe mixture was extracted with ether
  7. customto afford the crude aldehyde which
  8. customwas purified by column chromatography on silica gel
  9. washeluting with a 1:5 mixture of ethyl acetate

Sources & evidence

ORD record
ord-2795c3356de84b5b967b14a24b062563
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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