Ammonium Chloride → HCID 67996207, compound

HRID 2042952Notes

Reaction equation

HRID 2042952 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42][N:43]=3)[CH:32]=2)[O:11][C@@H:10]1[CH:49]=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:51][Mg]Br.[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42][N:43]=3)[CH:32]=2)[O:11][C@@H:10]1[CH:49]([OH:50])[CH3:51])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86680894HCID 86680894, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67996207HCID 67996207, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of aldehyde 101 (390 mg, 0.55 mmol) in THF (5.5 mL) was added methyl magnesiumbromide (3.0 M in ether, 0.28 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was poured into a saturated NH4Cl solution and then extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel column chromatography provided the desired secondary alcohol 103 (300 mg, 75%) as a solid. MH+723.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-f9decc94e97e462394f351c289a3eb11
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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