Hydrochloric Acid → HCID 11482946, compound

HRID 2424176Notes

Reaction equation

HRID 2424176 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13]C)[CH:12]=1)[C:9](=O)[CH:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH2:7][CH2:6]2.OC1C=C(OC)C=C2C=1C(=O)C(C1C=CC(OC)=CC=1)CC2.[BH4-].[Li+].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[CH:9]=[C:8]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 11381397HCID 11381397, compoundHCID 11392358HCID 11392358, compound

Product 1

HCID 11482946HCID 11482946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Synthesized from 6,8-dimethoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-naphthalen-1-one according to an analogous synthetic method to Preparation Example 192 described below, a solution of 8-hydroxy-6-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-naphthalen-1-one (6.2 g) in tetrahydrofuran (130 ml) was added dropwise to a suspension of lithium borohydride (1.1 g) in tetrahydrofuran (60 ml) on an ice bath, and the solution was stirred for 20 minutes at room temperature. To the reaction solution was added 2N hydrochloric acid on the ice bath, the solution was stirred, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-tetrahydrofuran system) to provide the title compound (5.6 g).

Workup

  1. stirringthe solution was stirred
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-tetrahydrofuran system)

Sources & evidence

ORD record
ord-578c0ed7252d44488d8f41922b50d56b
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

Loading…