Chloroacetyl chloride → HCID 21959306, compound

HRID 2055050Notes

Reaction equation

HRID 2055050 reaction equation
[CH3:1][Si:2]([CH3:45])([CH3:44])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=[CH:10][C:9]=1[C:23]1[C:24](=[O:43])[O:25][C:26]2[C:31]([C:32]=1[CH3:33])=[CH:30][CH:29]=[C:28]([O:34][CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:27]=2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:56][CH2:57][C:58](Cl)=[O:59]>C1COCC1.C(OCC)C>[CH3:45][Si:2]([CH3:44])([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[CH:11]=[CH:10][C:9]=1[C:23]1[C:24](=[O:43])[O:25][C:26]2[C:31]([C:32]=1[CH2:33][C:58](=[O:59])[CH2:57][Cl:56])=[CH:30][CH:29]=[C:28]([O:34][CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:27]=2

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 219592253-(2,4-Bis{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-4-methyl-7-{[2-(trimethylsilyl)ethoxy]methoxy}-2H-1-benzopyran-2-one

Product 1

HCID 21959306HCID 21959306, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

At room temperature, 3-[2,4-Bis-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-4-methyl-7-(2-trimethylsilanyl-ethoxymethoxy)-chromen-2-one (1.6 g, 2.37 mmol) in THF (10 mL) was added LiHMDS (2.9 mL, 2.84 mmol) slowly. The reaction mixture was stirred for 10 min and then added into chloroacetyl chloride (0.28 mL, 1.5 equiv.) in THF (20 mL) at −20° C. The reaction mixture was maintained at −20° C. for 1 hour, then diluted with diethyl ether (200 mL), washed with aqueous NH4Cl (100 ml), brine and organic layer was dried over anhydrous MgSO4. The resulting product was then concentration by vacuum to dryness and purified by silica gel column chromatography to yield the title compound as a colorless oil.

Workup

  1. washwashed with aqueous NH4Cl (100 ml), brine and organic layer
  2. dry with materialwas dried over anhydrous MgSO4
  3. concentrationconcentration by vacuum to dryness
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1ed11778ed645a5a2f15bda78140d93
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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