Hydrochloric Acid → HCID 11760910, compound

HRID 2306231Notes

Reaction equation

HRID 2306231 reaction equation
[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][C:25]2=[O:28])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][CH:25]2[OH:28])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 11047330HCID 11047330, compound

Product 1

HCID 11760910HCID 11760910, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-tert-butyldiphenylsilyloxy-1-indanone, as described above in Step A, (16.5 g, 42.7 mmol) in MeOH (500 mL) was added NaBH4 (3.2 g, 84.6 mmol) portionwise, over 5 min. The resulting mixture was stirred at ambient temperature for 1 hour, then cooled to 0° C. The chilled solution was adjusted to pH 4.5 with dilute aqueous HCl, then most of the MeOH was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (75 mL) and CHCl3 (150 mL). The organic layer was removed, and the aqueous phase was extracted further with CHCl3 (2×100 mL). The combined organic extracts were washed with brine, then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane—10% to EtOAc, to yield the titled product.

Workup

  1. temperaturecooled to 0° C
  2. custommost of the MeOH was removed under reduced pressure
  3. customThe residue was partitioned between saturated aqueous NaHCO3 (75 mL) and CHCl3 (150 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous phase was extracted further with CHCl3 (2×100 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with hexane—10% to EtOAc

Sources & evidence

ORD record
ord-b99922e6149744d690d6d1b8b27bcf26
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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