Methanol → HCID 69468650, compound

HRID 842938Notes

Reaction equation

HRID 842938 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH:9]1[CH3:12])=O)C.CO.[OH-].[Na+]>CCOCC>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:8]1([CH2:6][OH:5])[CH2:11][CH2:10][CH:9]1[CH3:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 68880526HCID 68880526, compound

Product 1

HCID 69468650HCID 69468650, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
23 °C

Procedure

Lithium borohydride (435 mg, 20 mmol) was added to a solution of ester 3 (2.3 g, 10 mmol) in Et2O (20 mL) at 0° C. After having stirred for 5 min, MeOH (640 mg, 20 mmol) was added dropwise and stirring continued at 0° C. until effervescence ceased. The mixture was warmed to 23° C. and was allowed to stir an additional hour, at which time the mixture was poured into 3N NaOH and stirred an additional 0.5 h. The organic layer was separated and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude alcohol 4 was purified by FCC (silica gel, 1:1, hexane/CH2Cl2).

Workup

  1. stirringstirring
  2. customcontinued at 0° C. until effervescence
  3. stirringto stir an additional hour, at which time the mixture
  4. stirringstirred an additional 0.5 h
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude alcohol 4 was purified by FCC (silica gel, 1:1, hexane/CH2Cl2)

Sources & evidence

ORD record
ord-f94593f9115e4a8ab9e22e6a63a3168b
Source dataset
uspto-grants-2002_04
Patent number
US06376533B1

Reaction notes

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