Hydrochloric Acid → HCID 136062924, compound

HRID 980760Notes

Reaction equation

HRID 980760 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]2[CH2:21][C:20](=[O:22])[C:19]([C:23](=O)[CH2:24][CH3:25])=[C:18]([OH:27])[CH2:17]2)=[C:4]2[C:9](=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13])[C:8](=[O:15])[CH2:7][CH2:6][CH2:5]2.Cl.[CH2:29]([O:31][NH2:32])[CH3:30].C([O-])(=O)C.[Na+].Cl>>[CH3:1][C:2]1[C:3]([CH:16]2[CH2:21][C:20](=[O:22])[C:19]([C:23](=[N:32][O:31][CH2:29][CH3:30])[CH2:24][CH3:25])=[C:18]([OH:27])[CH2:17]2)=[C:4]2[C:9](=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13])[C:8](=[O:15])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458879HCID 178458879, compound

Product 1

HCID 136062924HCID 136062924, compound

Procedure

A mixture of 5-(6,8-dimethyl-7-methoxy-1-oxo-1,2,3,4-tetrahydronaphth-5-yl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (0.48 g), ethoxyamine hydrochloride (1 equiv), anhydrous sodium acetate (1 equiv) and absolute alcohol (30 ml) was stirred at room temperature for 1 hr. The mixture was poured into a very dilute aqueous hydrochloric acid solution which was then immediately extracted with diethyl ether. The dried (MgSO4) organic fraction was evaporated to give 5-(6,8-dimethyl-7-methoxy-1-oxo-1,2,3,4-tetrahydronaphth-5-yl)-2[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one (6) as a pale yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.11-1.42 (6H,2xt); 1.9-3.8 (15H,m); 2.41 (3H,s); 2.52 (3H,s); 3.66 (3H,s); 4.14 (2H, q); OH not observed.

Workup

  1. extractionwas then immediately extracted with diethyl ether
  2. dry with materialThe dried (MgSO4) organic fraction
  3. customwas evaporated

Sources & evidence

ORD record
ord-e89854c02ce347db9efe2fd8d1ed38d1
Source dataset
uspto-grants-1987_01
Patent number
US04639267

Reaction notes

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