Hydrochloric Acid → HCID 68991126, compound

HRID 69507Notes

Reaction equation

HRID 69507 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:18]=[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])[S:16][C:15]=1[C:23]([OH:25])=[O:24].[CH2:26]=[O:27].Cl>C1COCC1.C(OCC)(=O)C.O>[OH:27][CH2:26][CH2:13][C:14]1[CH:18]=[C:17]([Si:19]([CH3:20])([CH3:21])[CH3:22])[S:16][C:15]=1[C:23]([OH:25])=[O:24]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7912DiisopropylamineHCID 68990463HCID 68990463, compoundHCID 178418339Butyllithium

Product 1

HCID 68991126HCID 68991126, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Diisopropylamine (9.4 g) was added to a solution of n-Butyllithium (1.6 M in hexane, 43.7 mL) in THF (67 mL) at −78° C. The mixture was stirred for 10 min at 0° C. and then cooled to −78° C. and a solution of 3-Methyl-5-trimethylsilanyl-thiophene-2-carboxylic acid (5.0 g) in THF (40 mL) was added. The mixture was stirred at −78° C. for 30 min and then paraformaldehyde (3.2 g) was added. After warming to room temperature water and ethyl acetate were added. The aqueous phase was slightly acidified with HCl (10%) and then extracted three time with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 244.39 (C10H16O3SSi); MS (ESI): 245 (M+H+).

Workup

  1. temperaturecooled to −78° C.
  2. stirringThe mixture was stirred at −78° C. for 30 min
  3. additionwere added
  4. extractionextracted three time with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customthe solvent was removed in vacuum
  7. customThe raw product was purified by preparative HPLC
  8. customIn this way the product was obtained with molecular weight 244.39 (C10H16O3SSi)

Sources & evidence

ORD record
ord-c013587275b3494eaf784ae761b7018e
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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