Allyl bromide → HCID 57463366, compound

HRID 253362Notes

Reaction equation

HRID 253362 reaction equation
[H-].[Na+].[OH:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5]1.[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:5]1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 14172791HCID 14172791, compound

Product 1

HCID 57463366HCID 57463366, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an atmosphere of argon, 12 g of sodium hydride (55-65%) are initially charged in 200 ml of abs. DMF, and the mixture is stirred at RT for 10 min. With ice-cooling, 54 g of benzyl (1S,3R)-3-hydroxycyclohex-1-yl ether in 70 ml of DMF are added dropwise. The mixture is stirred at RT for 90 min. With ice-cooling, 50 g of allyl bromide are slowly added dropwise. After the addition has ended, the mixture is stirred at 45° C. for 1 h. According to TLC, the reaction is complete. The reaction solution is quenched with 15 ml of iPrOH, diluted with water and sat. NaCl solution and extracted with MTBE. The combined organic phases are washed with water and NaCl solution, dried over MgSO4 and concentrated. This gives 60 g of benzyl (1S,3R)-3-allyloxycyclohex-1-yl ether as a light-beige oil. C16H22O2 (246.35), MS (ESI): 247 (M+H+).

Workup

  1. temperatureWith ice-cooling
  2. temperatureWith ice-cooling
  3. additionAfter the addition
  4. stirringthe mixture is stirred at 45° C. for 1 h
  5. customThe reaction solution is quenched with 15 ml of iPrOH
  6. additiondiluted with water and sat. NaCl solution
  7. extractionextracted with MTBE
  8. washThe combined organic phases are washed with water and NaCl solution
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-917bf8f84ae248e5b812a23e4405aa65
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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