Tetrahydrofuran → HCID 86702588, compound

HRID 1746820Notes

Reaction equation

HRID 1746820 reaction equation
O1CCCC1.[O:6]=[C:7]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8]P(=O)(OC)OC.[H-].[Na+].[CH:25]([C@@H:27]1[C@@H:35]2[C@@H:30]([S:31][C@@H:32]([CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH2:33][CH2:34]2)[CH2:29][C@H:28]1[O:43][CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][O:45]1)=O>C(OCC)(=O)C.C(O)(=O)C>[O:6]=[C:7]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)/[CH:8]=[CH:25]/[C@@H:27]1[C@@H:35]2[C@@H:30]([S:31][C@@H:32]([CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH2:33][CH2:34]2)[CH2:29][C@H:28]1[O:43][CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][O:45]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 580104Dimethyl 2-oxo-3-phenoxypropylphosphonateHCID 86702587HCID 86702587, compound

Product 1

HCID 86702588HCID 86702588, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an anhydrous tetrahydrofuran (2.7 mL) solution of dimethyl (2-oxo-3-phenoxypropyl)phosphonate (194 mg) was added sodium hydride (24.8 mg) in an ice bath, and the mixture was stirred at room temperature for 1.5 hours. Thereto was added dropwise an anhydrous tetrahydrofuran (2 mL) solution of the compound 11 (200 mg), and the mixture was reacted at room temperature for 4.5 hours. Acetic acid was added in a small amount, and the reaction liquid was then diluted with ethyl acetate. This solution was washed with water and a saturated saline, dried with anhydrous magnesium sulfate, and then concentrated to obtain a titled compound (250 mg) having the following physical property values.

Workup

  1. customthe mixture was reacted at room temperature for 4.5 hours
  2. customthe reaction liquid
  3. washThis solution was washed with water
  4. dry with materiala saturated saline, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9d616efaf9a44d0ea2cfe44558c498be
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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