Sodium borohydride → HCID 58692119, compound

HRID 269459Notes

Reaction equation

HRID 269459 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[C:6]2=O.C1COCC1.CO.[BH4-].[Na+]>O>[Cl:11][C:9]1[CH:8]=[C:7]2[C:3](=[C:2]([Cl:1])[CH:10]=1)[CH2:4][C:5]([CH3:13])=[CH:6]2

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuranHCID 221734804,6-Dichloro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 58692119HCID 58692119, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 29.3 g (0.136 mol) of 4,6-dichloro-2-methylindan-1-one in 370 ml of a mixture of THF-methanol (2:1, vol.), 11.8 g (0.312 mol) of NaBH4 was added in small portions, while vigorously stirring, over 2 h at 0° C. This mixture was stirred for 12 h at room temperature and then added to 1000 ml of cold water. The organic layer was separated, the aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. The residue was dissolved in 700 ml of toluene, and 2.0 g of p-TosOH was added. The resulting solution was refluxed for 4 h using a Dean-Stark trap to remove the water formed, and then it was passed through a short Silica Gel 60 column (40-63 um, d 100 mm, l 80 mm, eluent: hexanes). This column was additionally washed with 250 ml of toluene. The combined organic fractions were evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 60 mm, l 150 mm). Yield 24.6 g (91%).

Workup

  1. stirringThis mixture was stirred for 12 h at room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×300 ml of methyl-tert-butyl ether
  4. dry with materialThe combined organic fractions were dried over K2CO3
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in 700 ml of toluene
  7. addition2.0 g of p-TosOH was added
  8. temperatureThe resulting solution was refluxed for 4 h
  9. customto remove the water
  10. customformed
  11. washThis column was additionally washed with 250 ml of toluene
  12. customThe combined organic fractions were evaporated to dryness
  13. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 60 mm, l 150 mm)

Sources & evidence

ORD record
ord-bda5a1fc03854d04a78ff238b5d32880
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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