Hydrochloric Acid → HCID 14281435, compound

HRID 2231886Notes

Reaction equation

HRID 2231886 reaction equation
C([Li])CCC.[Si:6]([O:13][CH:14]([C:44]1[N:45]=[CH:46][O:47][CH:48]=1)[CH2:15][CH:16]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:17]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH:18]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH3:19])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH:49]([C:51]1[O:55][CH:54]=[N:53][CH:52]=1)=[O:50].Cl>CCCCCC.C1COCC1.O>[O:55]1[C:51]([CH:49]([C:46]2[O:47][CH:48]=[C:44]([CH:14]([O:13][Si:6]([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:7])[CH3:8])[CH2:15][CH:16]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:38])[CH3:39])[CH:17]([O:28][Si:29]([C:32]([CH3:33])([CH3:34])[CH3:35])([CH3:31])[CH3:30])[CH:18]([O:20][Si:21]([C:24]([CH3:26])([CH3:25])[CH3:27])([CH3:23])[CH3:22])[CH3:19])[N:45]=2)[OH:50])=[CH:52][N:53]=[CH:54]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 118293725-OXAZOLECARBOXALDEHYDEHCID 14281434HCID 14281434, compoundHCID 178418339Butyllithium

Product 1

HCID 14281435HCID 14281435, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

Butyllithium (n-Buli, 0.32 g, 5 mmol) in hexane is added to a -50° C. Solution of 4-[1,3,4,5-tetra(t-butyldimethylsilyloxy)hexyl]oxazole (6, 3.4 g, 5 mmol) in THF (50 mL). The resulting solution stirred at -50° C. for three hours. A solution of 5-formyloxazole (0.53 g, 5.5 mmol - Preparation 20) in THF (7 mL) is added, and the mixture allowed to warm to room temperature while stirring for 12 hours. The resulting mixture is added to water, acidified with HCl and extracted three times with ether. The organic layer is washed with aqueous Na2SO3 and brine, dried over Na2SO4, and evaporated to yield 2-[1-(oxazol-5-yl)-1-hydroxymethyl]-4-[1,3,4,5-tetra(t-butyldimethylsilyloxy)hexyl]oxazole (7).

Workup

  1. temperatureto warm to room temperature
  2. stirringwhile stirring for 12 hours
  3. extractionextracted three times with ether
  4. washThe organic layer is washed with aqueous Na2SO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-3fdd377b95fb4605b79b837648809c90
Source dataset
uspto-grants-1988_11
Patent number
US04785012

Reaction notes

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