Methanol → HCID 15460468, compound

HRID 2187353Notes

Reaction equation

HRID 2187353 reaction equation
C1COCC1.C([O:9][CH2:10][CH2:11][O:12][C@H:13]1[C@H:45]([O:46][Si:47]([CH2:52][CH3:53])([CH2:50][CH3:51])[CH2:48][CH3:49])[C@@:44]2([CH3:54])[C:16](=[CH:17][CH:18]=[C:19]3[C@@H:43]2[CH2:42][CH2:41][C@@:40]2([CH3:55])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C@H:24]([CH3:39])[CH2:25][CH2:26][CH2:27][C:28]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])([CH3:30])[CH3:29])[CH2:15][C@H:14]1[O:56][Si:57]([CH2:62][CH3:63])([CH2:60][CH3:61])[CH2:58][CH3:59])(=O)C.CO.[OH-].[K+]>O.C(O)(=O)C>[OH:9][CH2:10][CH2:11][O:12][C@H:13]1[C@H:45]([O:46][Si:47]([CH2:48][CH3:49])([CH2:50][CH3:51])[CH2:52][CH3:53])[C@@:44]2([CH3:54])[C:16](=[CH:17][CH:18]=[C:19]3[C@@H:43]2[CH2:42][CH2:41][C@@:40]2([CH3:55])[C@H:20]3[CH2:21][CH2:22][C@@H:23]2[C@H:24]([CH3:39])[CH2:25][CH2:26][CH2:27][C:28]([O:31][Si:32]([CH2:35][CH3:36])([CH2:33][CH3:34])[CH2:37][CH3:38])([CH3:29])[CH3:30])[CH2:15][C@H:14]1[O:56][Si:57]([CH2:58][CH3:59])([CH2:60][CH3:61])[CH2:62][CH3:63]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15460467HCID 15460467, compound

Product 1

HCID 15460468HCID 15460468, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

To a THF (5 ml) solution of compound 4 (327 mg, 380 μmol) obtained in Example 2, a methanol (10 ml) solution of potassium hydroxide (72 mg, 1.29 mmol) was added, and the mixture was stirred in an argon atmosphere for 1.5 hours at 15 to 30° C. To the reaction mixture, acetic acid (150 μl) was added. Then, the resulting mixture was poured into water, extracted twice with a solvent mixture of ethyl acetate and hexane (1:1), and washed with a saturated solution of sodium carbonate and a saturated aqueous solution of sodium chloride in this order. The organic phase was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by flash column chromatography (8% ethyl acetate/hexane) to give colorless oily compound 5 (173 mg, 56%).

Workup

  1. extractionextracted twice with a solvent mixture of ethyl acetate and hexane (1:1)
  2. washwashed with a saturated solution of sodium carbonate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by flash column chromatography (8% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4edbe1540f37465782f39bc983e277ed
Source dataset
uspto-grants-2002_06
Patent number
US06410523B1

Reaction notes

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