Hydrochloric Acid → HCID 10112471, compound

HRID 1957691Notes

Reaction equation

HRID 1957691 reaction equation
[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]23[CH2:32][CH:27]4[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]4)[CH2:24]2)[CH2:30]3)[CH:16]=1)[C:3]#[C:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][CH:6]=1.C1COCC1.[OH-].[Li+].Cl>O>[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]23[CH2:24][CH:25]4[CH2:31][CH:29]([CH2:28][CH:27]([CH2:26]4)[CH2:32]2)[CH2:30]3)[CH:16]=1)[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19068299HCID 19068299, compound

Product 1

HCID 10112471HCID 10112471, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

962 mg (2.2 mmol) of the above methyl ester (b) and 10 ml of THF were introduced into a round-bottomed flask and 283 mg (6.7 mmol) of lithium hydroxide were added. The reaction medium was heated at reflux for 5 hours and was then poured into water and acidified to pH 1 with concentrated hydrochloric acid. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The solid obtained was triturated from hexane, filtered off and dried. 600 mg (85%) of the expected acid, having a melting point of 232°-4° C., were recovered.

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureat reflux for 5 hours
  3. customThe organic phase was separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe solid obtained
  7. customwas triturated from hexane
  8. filtrationfiltered off
  9. customdried
  10. customwere recovered

Sources & evidence

ORD record
ord-3b43635fbfbc4b82a79083ad0b3a4a09
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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