Benzyl Bromide → HCID 14484895, compound

HRID 1089609Notes

Reaction equation

HRID 1089609 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]([OH:16])=[CH:14][C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=1.[H][H].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.CCCCCC>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]([O:16][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydride2×HCID 14484893HCID 14484893, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14484895HCID 14484895, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.678 g, 16.95 mmol) was washed with petroleum ether then suspended in dry tetrahydrofuran (15 mL) and cooled in an icebath. A solution of 6 (3.00 g, 15.4 mmol) in dry tetrahydrofuran (16 mL) was added dropwise to the sodium hydride suspension. When the hydrogen evolution had ceased, benzyl bromide (3.03 g, 17.7 mmol) was added dropwise and the mixture allowed to stir at room temperature overnight. The reaction was diluted with hexane (20 mL), filtered, and the filtrate concentrated. The residue was taken up in ether (50 mL), washed with 2N HCl and brine, dried (MgSO4) and concentrated to give 7.

Workup

  1. temperaturecooled in an icebath
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. washwashed with 2N HCl and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give 7

Sources & evidence

ORD record
ord-b0d2f50119994a2ba4e5811fe7684f58
Source dataset
uspto-grants-1990_10
Patent number
US04966907

Reaction notes

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