Methanesulfonyl chloride → Tert-butyl {3-[4-(chloromethyl)-3-methoxyphenoxy]propoxy}dimethylsilane

HRID 2207082Notes

Reaction equation

HRID 2207082 reaction equation
CS(Cl)(=O)=O.[Si:6]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[C:20]([O:26][CH3:27])[CH:19]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C.[Cl-:37].[Li+]>C1COCC1.O.[Cl-].[Na+].O>[C:9]([Si:6]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][Cl:37])=[C:20]([O:26][CH3:27])[CH:19]=1)([CH3:8])[CH3:7])([CH3:12])([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 68747805(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxyphenyl)methanol

Product 1

HCID 123781615Tert-butyl {3-[4-(chloromethyl)-3-methoxyphenoxy]propoxy}dimethylsilaneYield 111.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Methanesulfonyl chloride (4.02 mL) was added to the mixture of the product from step (ii) (8.47 g), diisopropylethylamine (13.4 mL) and lithium chloride (3.29 g) in THF (105 mL) at RT and stirred for 40 mins. The mixture was diluted with water and brine, and extracted with EtOAc. The combined organic solutions were washed with brine, dried and concentrated to give 10.0 g of the subtitle compound as a yellow oil; 1H NMR: 7.23 (1H, dd), 6.44-6.49 (2H, m), 4.63 (2H, s), 4.06 (2H, t), 3.85 (3H, s), 3.79 (2H, t), 1.94-2.02 (2H, m), 0.89 (9H, s), 0.04 (6H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic solutions were washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93fc405323ad468e9c033d5c7fed2397
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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