Methanol → HCID 10602695, compound

HRID 2211306Notes

Reaction equation

HRID 2211306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14](=[O:31])[CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[O:18])[CH:6]=[C:7]([I:13])[C:8]=1[O:9][CH2:10][CH2:11][OH:12].O1CCCC1.CO.[BH4-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([OH:31])[CH2:15][CH2:16][CH:17]([C:19]2[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=2)[OH:18])[CH:6]=[C:7]([I:13])[C:8]=1[O:9][CH2:10][CH2:11][OH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10530575HCID 10530575, compound

Product 1

HCID 10602695HCID 10602695, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(3-Methoxy-4-hydroxyethoxy-5-iodophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione (11.6 g, 21.3 mmol), was added to 120 mL tetrahydrofuran and 240 mL methanol. To this solution was added dropwise sodium borohydride (1.45 g, 38.4 mmol), in 60 mL water. The reaction mixture was stirred at room temperature for 2.5 hours, and then cooled, quenched with water, and the aqueous layer extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to provide the product (11.8 g, 98.8%). 1H NMR (CDCl3) δ1.84 (m, 4H); 3.84 (m, 2H); 3.86 (s, 3H); 3.87 (s, 9H); 4.15 (t, 2H); 4.68 (m, 2H); 6.57 (s, 2H); 6.91 (s, 1H); 7.32 (s, 1H).

Workup

  1. temperaturecooled
  2. customquenched with water
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f8e974d1b9374866b942ee226c72d43c
Source dataset
uspto-grants-1995_10
Patent number
US05463083

Reaction notes

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