Hydrochloric Acid → HCID 11808157, compound

HRID 974720Notes

Reaction equation

HRID 974720 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.C(OCC)(=O)C.O.CCCCCC.CN(C=O)C>[Si:13]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 12575Isovanillic AcidHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11808157HCID 11808157, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-4-methoxybenzoic acid (6.726 g, 40 mmol), tert-butyldimethylsilyl chloride (13.26 g, 88 mmol), imidazole (10.893 g, 160 mmol) and DMF (40 mL) was stirred at room temperature for 18 hr. Hexane was added and the resulting mixture washed with water. The aqueous layer was reextracted two times with hexane and the extracts added to the hexane layer from the first extraction. The combined extracts were washed with small amount of water. During the washing some precipitate formed. The organic phase, together with the precipitate, was dissolved in small amount of methanol and rotary evaporated. The residue was taken into methanol (100 ml) and stirred at room temperature with potassium carbonate (10 g) and water (3 ml) for 1.5 hr. A mixture of ethyl acetate and crushed ice was added and the mixture was carefully acidified with dilute hydrochloric acid (the final pH of the aqueous layer was 3.5). The organic phase was separated and the aqueous layer extracted two times with ethyl acetate. The combined extracts were washed with a mixture of brine and water (1:1) and dried. TLC (silica gel, hexane/ethyl acetate=2:1) of the product gave one spot having an Rf of 0.2. NMR(δ): 0.18 (s, 6H), 1.00 (s, 9H), 3.90 (s, 3H).

Workup

  1. washthe resulting mixture washed with water
  2. additionthe extracts added to the hexane layer from the first extraction
  3. washThe combined extracts were washed with small amount of water
  4. customDuring the washing some precipitate formed
  5. customcrushed ice
  6. additionwas added
  7. customThe organic phase was separated
  8. extractionthe aqueous layer extracted two times with ethyl acetate
  9. washThe combined extracts were washed with a mixture of brine and water (1:1)
  10. customdried
  11. customTLC (silica gel, hexane/ethyl acetate=2:1) of the product gave one spot

Sources & evidence

ORD record
ord-6730c1eae91f436f97bcab8d9d5741ef
Source dataset
uspto-grants-1997_03
Patent number
US05607625

Reaction notes

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