Lithium Hexamethyldisilazide → HCID 58380839, compound

HRID 1948150Notes

Reaction equation

HRID 1948150 reaction equation
[CH2:1]([C:3]1([CH:13]=[N:14][S:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1)[CH3:2].C(C1(C#N)CCC2(OCCO2)CC1)C.C1(CC2(C=NS(C(C)(C)C)=O)CCC3(OCCO3)CC2)CC1.[F:57][CH2:58][S:59]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)(=[O:61])=[O:60].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[C:62]1([S:59]([CH:58]([F:57])[CH:13]([NH:14][S:15]([C:17]([CH3:19])([CH3:18])[CH3:20])=[O:16])[C:3]2([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]3([O:7][CH2:8][CH2:9][O:10]3)[CH2:11][CH2:12]2)(=[O:61])=[O:60])[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

7

Reactant 5

HCID 2733832Lithium HexamethyldisilazideHCID 2759036Fluoromethyl Phenyl SulfoneHCID 67072565HCID 67072565, compoundHCID 67072577HCID 67072577, compoundHCID 67072583HCID 67072583, compound

Product 1

HCID 58380839HCID 58380839, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.70 g (5.64 mmol) of 2-methyl-propane-2-sulfinic acid 1-(8-ethyl-1,4-dioxa-spiro[4.5]dec-8-yl)methylideneamide (prepared from 8-ethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile using the protocol described for the synthesis of 19) and 982 mg (5.64 mmol) of fluoromethyl-phenyl sulfone in 60 mL of abs. tetrahydrofuran were added at −78° C. 5.92 mL (5.92 mmol) of a 1M solution of lithiumbis(trimethylsilyl)amide in tetrahydrofuran. The mixture was stirred for 1 h at −78° C. before being quenched by addition of saturated aqueous ammonium chloride solution and extracted twice with 100 mL of ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo to give 2.65 g of the crude title compound. Rt=0.91 min (Method P). Detected mass: 476.4 (M+H+)

Workup

  1. custombefore being quenched by addition of saturated aqueous ammonium chloride solution
  2. extractionextracted twice with 100 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ee834f0d887420da8026a8923d104b0
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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