Lithium Hydroxide → HCID 70157235, compound

HRID 278540Notes

Reaction equation

HRID 278540 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][C@@H:12]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C@@H:11]1[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].[Li+].[OH-]>C1COCC1>[Si:31]([O:30][CH2:29][C@H:11]1[C@H:12]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:13][C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C@@H:10]1[CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][C:3]([OH:38])=[O:2])([C:34]([CH3:37])([CH3:35])[CH3:36])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70158929HCID 70158929, compound

Product 1

HCID 70157235HCID 70157235, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (Z)-7-[(1R,2S,3R,5S)-2-(tert-Butyldimethylsilanyloxymethyl)-3,5-bis-(tetrahydropyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester (1.5 g, 2.71 mmol) stirring in THF was added LiOH (4 mL, 1M in H2O, 4.0 mmol) and the stirring was continued at 23° C. for 12 h. The THF was evaporated and the mixture was acidified with cold 1% HCl and extracted with CH2Cl2 (3×). The combined organics were washed with brine, dried (Na2SO4) filtered and concentrated in vacuo. FCC (silica gel, 30% EtOAc/hex) afforded 1.23 g of the above named acid.

Workup

  1. customThe THF was evaporated
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customFCC (silica gel, 30% EtOAc/hex) afforded 1.23 g of the

Sources & evidence

ORD record
ord-5fa1d1b7678f437483836d1d079ff706
Source dataset
uspto-grants-2002_03
Patent number
US06359181B1

Reaction notes

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