Hydrochloric Acid → HCID 86733227, compound

HRID 1605497Notes

Reaction equation

HRID 1605497 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:44])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:43])[CH:16]([OH:42])[CH:17]([CH3:41])[C:18](=[O:40])[CH:19]([CH2:38][CH3:39])[CH:20]2[CH:24]([CH3:25])[CH2:23][C:22]([CH2:36][CH3:37])([CH:26]3[CH2:31][CH2:30][C:29]([CH2:33][CH3:34])([OH:32])[CH:28]([CH3:35])[O:27]3)[O:21]2)=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:45].[Na].Cl.[N+](=[CH2:50])=[N-]>CCOCC>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:44])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:43])[CH:16]([OH:42])[CH:17]([CH3:41])[C:18](=[O:40])[CH:19]([CH2:38][CH3:39])[CH:20]2[CH:24]([CH3:25])[CH2:23][C:22]([CH2:36][CH3:37])([CH:26]3[CH2:31][CH2:30][C:29]([CH2:33][CH3:34])([OH:32])[CH:28]([CH3:35])[O:27]3)[O:21]2)=[C:4]([C:5]([O:7][CH3:50])=[O:6])[C:3]=1[OH:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 5360545SodiumHCID 70626317HCID 70626317, compound

Product 1

HCID 86733227HCID 86733227, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.344 g (2 mole) of 3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}acetyl salicylic acid, sodium salt was treated with ether (30 ml) and 1N HCl (30 ml). The mixture was shaken in a separatory funnel until all the starting material had dissolved. The ether layer was then washed twice with water and treated with 20 ml solution of ethereal diazomethane (5 mmole). After drying (Na2SO4), the solution was evaporated to give 3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}acetyl salicylic acid, methyl ester as an oil, [α]D25 +0.99° (1% in methanol).

Workup

  1. dissolutionhad dissolved
  2. washThe ether layer was then washed twice with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-53b852fefc4a43659eb86a0abcdd1c72
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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