Sodium hydride → HCID 14422727, compound

HRID 1276301Notes

Reaction equation

HRID 1276301 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[O:27][CH2:26][CH2:25][CH:24](Br)[C:23](=[O:29])[C:22]=2[CH:30]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[O:27][CH2:26][CH2:25][CH:24]([O:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:23](=[O:29])[C:22]=2[CH:30]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77195CyclopentanemethanolHCID 14422726HCID 14422726, compound

Product 1

HCID 14422727HCID 14422727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.5 g of (cyclopentyl)methanol in 50 ml of tetrahydrofuran is added 720 mg of 50% sodium hydride. After stirring until evolution of H2 is substantially complete (about 30 minutes), a solution of 4.5 g of crude 7-benzyloxy-4-bromo-3,4-dihydro-1-benzoxepin-5 (2H)-one is added. The reaction is allowed to stir at room temperature for 5 hours. The tetrahydrofuran is evaporated in vacuo, and the residue dissolved in ethyl acetate and washed with water. The ethyl acetate layer is dried over sodium sulfate and evaporated in vacuo to yield present title product.

Workup

  1. custom(about 30 minutes)
  2. stirringto stir at room temperature for 5 hours
  3. customThe tetrahydrofuran is evaporated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe ethyl acetate layer is dried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f44ffa3f8d7243a8867bd7c87531aca8
Source dataset
uspto-grants-2000_12
Patent number
US06166031

Reaction notes

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