Hydrochloric Acid → HCID 9867075, compound

HRID 1872860Notes

Reaction equation

HRID 1872860 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([C:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][C:17]=3[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:29].CO.Cl>O>[Br:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][C:17]=3[CH2:25][CH2:26][CH2:27][CH3:28])[OH:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 10526273HCID 10526273, compound

Product 1

HCID 9867075HCID 9867075, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.33 g, 8.98 mmol) was added into a mixture of 1-bromo-6-(2-butyl-benzofuran-3-carbonyl)-naphthalen-2-ol (1.9 g, 4.49 mmol) and methyl alcohol (10 mL). The reaction mixture was stirred for 1 hour poured into water, acidified with HCl (2 N) and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtOAc 2:1) gave an off-white solid(1.65 g): MS m/e 424 (M+);

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtOAc 2:1)

Sources & evidence

ORD record
ord-a5a30d7fa0ea4b858bf660c4354b468b
Source dataset
uspto-grants-2000_08
Patent number
US06110963

Reaction notes

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