Methanol → HCID 12080540, compound

HRID 1355635Notes

Reaction equation

HRID 1355635 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1([CH2:12][C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)=O)C.CO.[OH-].[Na+]>CCOCC>[Cl:18][C:15]1[S:14][C:13]([CH2:12][C:8]2([CH2:6][OH:5])[CH2:11][CH2:10][CH2:9]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 12080539HCID 12080539, compound

Product 1

HCID 12080540HCID 12080540, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
23 °C

Procedure

Lithium borohydride (718 mg, 33 mmol) was added to a solution of ester 19 (2.9 g, 11.2 mmol) in ether (50 mL) at 0° C. After having stirred for 5 min, MeOH (1.05 g, 33 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 NaOH (3N) and stirred. The organic layer was seperated and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified via FCC (silica gel, 1:1, hexane/CH2Cl2) to give 2.57 g of the above named alcohol 20.

Workup

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

Sources & evidence

ORD record
ord-00caed68d47a45e2b1b2914477e62f2f
Source dataset
uspto-grants-2003_07
Patent number
US06586462B2

Reaction notes

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