(Diethylamino)sulfur trifluoride → HCID 22258131, compound

HRID 1611000Notes

Reaction equation

HRID 1611000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25](O)[C:26]([OH:28])=[O:27].C(N(S(F)(F)[F:36])CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25]([F:36])[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 9932554HCID 9932554, compound

Product 1

HCID 22258131HCID 22258131, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Example 1 Part B compound (461 mg, 1.00 mmol) in CH2Cl2 (10 mL) under argon at 0° C. was added a solution of diethylaminosulfur trifluoride [DAST] (265 μL, 2.0 mmol) in CH2Cl2 (5 mL) over 20 min. The reaction mixture was stirred for an additional 45 min, then quenched with saturated sodium bicarbonate solution and extracted twice with CH2Cl2. The extracts were combined, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a light yellow oil, 218 mg (47% yield). LC/MS gave the correct molecular ion [(M+H)+=463] for the desired compound.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. extractionextracted twice with CH2Cl2
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-621b7190be764e10a085cd72402042be
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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