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Hydrochloric Acid → HCID 86741996, compound

HRID 1032743
Notes
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Reaction equation

HRID 1032743 reaction equation
[OH:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:21])/[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[S:17])=[C:9]([O:22][CH3:23])[C:8]([CH3:24])=[C:7]2[C:3]=1[C:4](=[O:25])[O:5][CH2:6]2.N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33].Cl>C(#N)C>[C:32]([O:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:21])/[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[S:17])=[C:9]([O:22][CH3:23])[C:8]([CH3:24])=[C:7]2[C:3]=1[C:4](=[O:25])[O:5][CH2:6]2)(=[O:34])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 86741995HCID 86741995, compound

Product 1

HCID 86741996HCID 86741996, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.6 g of ethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate in 120 ml of acetonitrile at 0° C. was added 0.74 ml of pyridine followed by 1.0 ml of acetyl chloride. After stirring for 2 hours the reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and evaporated to an oil, which was triturated with ether to give ethyl (E)-6-(1,3-dihydro-4-acetoxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-thiohexenoate, m.p. 81°-84° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  3. customevaporated to an oil, which
  4. customwas triturated with ether

Sources & evidence

ORD record
ord-a6f9d3b73a0d4c77a06a013d32830bf4
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04959387

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes