Water → trans-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene

HRID 501698Notes

Reaction equation

HRID 501698 reaction equation
[N:1]([CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH:5]1[OH:15])=[N+:2]=[N-:3].[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20].O>CN(C=O)C>[CH2:20]([O:15][C@@H:5]1[CH2:6][C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C@H:4]1[N:1]=[N+:2]=[N-:3])[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86622330(1RS,2RS)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 86622329trans-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step AA (5): To a solution of (1RS,2RS)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol (64 mg) from Step AA (4) in DMF (0.30 mL) at rt was added sodium hydride (95% purity, 20 mg), and the resulting mixture was stirred at rt for 5 min. Allyl bromide (40 μL) was added, and the reaction mixture was stirred for 5 min. Water was added, the aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give trans-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene as a slightly yellowish oil (71 mg). 1H NMR (400 MHz, CDCl3) δ 7.09 (1H, d), 6.84 (2H, m), 5.96 (1H, m), 5.34 (1H, d), 5.23 (1H, d), 4.75 (1H, d), 4.23 (1H, q), 4.16 (2H, q), 3.80 (3H, s), 3.21 (1H, dd), 2.78 (1H, dd).

Workup

  1. stirringthe reaction mixture was stirred for 5 min
  2. extractionthe aqueous layer was extracted with EtOAc (×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6a1c1f0cdeec463c88100c95cb23878b
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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