Benzyl Chloride → HCID 90254651, compound

HRID 1175217Notes

Reaction equation

HRID 1175217 reaction equation
[OH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH2:15][Si](C)(C)C)=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.[H-].[Na+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][C:15]3[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=3)=[O:12])[CH:9]=2)[CH2:4][CH2:3]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 68691308HCID 68691308, compound

Product 1

HCID 90254651HCID 90254651, compound

Procedure

To a solution of the alcohol from Step 2 (140 mg, 0.503 mmol) was added NaH (28.2 mg, 1.18 mmol) in one portion at RT. After stirring for 30 min, BnCl (116 μL, 1.01 mmol) was added dropwise and the resulting mixture was stirred overnight. The excess NaH was quenched with water and the mixture was transferred to a seperatory funnel where the aqueous layer was washed 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated to yield an oil. The title compound was purified on a Biotage MPLC (grad: 100% Hex to 60% EtOAc in Hex).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customThe excess NaH was quenched with water
  3. customthe mixture was transferred to a seperatory funnel
  4. washwhere the aqueous layer was washed 3× with DCM
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil
  9. customThe title compound was purified on a Biotage MPLC (grad: 100% Hex to 60% EtOAc in Hex)

Sources & evidence

ORD record
ord-ff99a3f7101249ccbf4b81043b9e235a
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

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