Water → HCID 11697580, compound

HRID 636265Notes

Reaction equation

HRID 636265 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([O:8]C(=O)C)[C@@H:5]([CH3:12])[C@@H:4]([O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:3]1.[C:31]([O-])([O-])=[O:32].[K+].[K+].O.CC[O:40]CC>CO>[Si:14]([O:13][C@@H:4]1[C@H:5]([CH3:12])[C@H:6]([OH:8])[CH2:7][C@H:2]([C:1]([O:32][CH3:31])=[O:40])[CH2:3]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 11430Potassium Carbonate2×HCID 90911886HCID 90911886, compound

Product 1

HCID 11697580HCID 11697580, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2.1.c (R=Me, P=TBDPS, A=COOCH3) (392 mg, 0.992 mmol) in 10 ml of dry MeOH at room temperature was added dry K2CO3 (30 mg). After 10 min., a second portion of K2CO3 (19 mg) (total: 49 mg, 0.496 mmol) was added. The mixture was stirred for 6 h, then poured into water and Et2O (70 ml:50 ml). The organic layer was separated and the aqueous layer was extracted with Et2O (50 ml×3) and dried over MgSO4. Separation by flash chromatography on silica (isooctane/EtOAc) 9:1), gave hydroxy compound 2.2.c (R=Me, P=TBDPS, A=COOCH3) (344 mg, 98%) as a colorless oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with Et2O (50 ml×3)
  3. dry with materialdried over MgSO4
  4. customSeparation by flash chromatography on silica (isooctane/EtOAc) 9:1),

Sources & evidence

ORD record
ord-039ea08fc420472d83dba2d4c39fbda1
Source dataset
uspto-grants-2001_02
Patent number
US06191292B1

Reaction notes

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