Hydrochloric Acid → HCID 19372339, compound

HRID 129695Notes

Reaction equation

HRID 129695 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:21]([O:23][CH3:24])=[O:22])[CH:4]=1)=[CH2:2].[OH-:25].[Na+].OO.Cl>C1COCC1.O>[OH:25][CH:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:21]([O:23][CH3:24])=[O:22])[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 19372293HCID 19372293, compound

Product 1

HCID 19372339HCID 19372339, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 0.3 g (0.9 mmol) of 1-vinyl-3-carbomethoxy-6benzyloxynaphthalene and 0.9 ml (0.9 mmol) of 1.0M BH3.THF complex in 15 ml of THF is stirred at 25° C. for 2 hours. To this is added 1 ml of H2O, 1 ml of 1N NaOH and 1 ml of 30% H2O2 which is then stirred at 25° C. for 2 hours. The mixture is acidified to pH ~1 using 1N HCl and extracted with ethyl acetate. The organics are dried (MgSO4) and concentrated in vacuo. Purification by flash silica gel chromatography using 15% ethyl acetate in hexanes as an eluent affords 0.08 g of 1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene in the form a yellow oil which is used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics are dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-2a97058160b440d5925a3d601fdfd9e5
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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