Hydrochloric Acid → HCID 20250470, compound

HRID 1285260Notes

Reaction equation

HRID 1285260 reaction equation
[BH4-].[Li+].C(C1C=CC=CC=1O[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:24]([CH2:25][CH2:26][CH3:27])=[C:23]2[C:18]([C:19](=O)[CH2:20][CH:21]([C:28]([OH:30])=O)[O:22]2)=[CH:17][CH:16]=1)CC.[BH4-].Cl.[CH3:38][CH2:39]OCC>O>[OH:30][CH2:28][CH:21]1[CH2:20][CH2:19][C:18]2[C:23](=[C:24]([CH2:25][CH2:26][CH3:27])[C:15]([O:14][CH2:13][C:12]3[CH:11]=[CH:10][CH:9]=[CH:39][CH:38]=3)=[CH:16][CH:17]=2)[O:22]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 28123BorohydrideHCID 4148881Lithium borohydrideHCID 20250463HCID 20250463, compound

Product 1

HCID 20250470HCID 20250470, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3 neck 250 ml round bottom flask fitted with a magnetic stirring bar, a dropping funnel, a gas inlet tube, and a glass stopper was flame dried and flushed with argon. 100 ml of dry ether was introduced and 331 mg (15.2 mmole) of lithium borohydride was added to the ether. A solution of 5.17 g (15.2 mmole) of the compound of Example 32 in 50 ml of ether was added dropwise to the stirred slurry of borohydride. After the addition was completed, the solution was stirred for 2 hours additional at room temperature. The flask was cooled in an ice bath and 20 ml of water added dropwise followed by the careful dropwise addition of dilute hydrochloric acid until the solution cleared. The aqueous layer was drained off in a separatory funnel and the ether washed once with saturated sodium bicarbonate solution and then with brine. Drying the ether with anhydrous magnesium sulfate, filtration to separate the drying agent and ether removal by rotary evaporation gave 4.34 g (91%) of the title compound as an oil. Calc: C, 76.89; H, 7.74; Found: C, 76.75; H, 7.66.

Workup

  1. customA 3 neck 250 ml round bottom flask fitted with a magnetic stirring bar, a dropping funnel, a gas inlet tube
  2. temperaturea glass stopper was flame
  3. customdried
  4. customflushed with argon
  5. addition100 ml of dry ether was introduced
  6. additionAfter the addition
  7. temperatureThe flask was cooled in an ice bath
  8. customThe aqueous layer was drained off in a separatory funnel
  9. washthe ether washed once with saturated sodium bicarbonate solution
  10. dry with materialDrying the ether
  11. filtrationwith anhydrous magnesium sulfate, filtration
  12. customto separate
  13. customthe drying agent and ether removal
  14. customby rotary evaporation

Sources & evidence

ORD record
ord-b872d62bc6664f72a410caea92888684
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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