Dabco → HCID 86591009, compound

HRID 398192Notes

Reaction equation

HRID 398192 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C1N2CCN(CC2)C1.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[S:28]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:27](=[S:28])[N:26]([CH3:30])[CH3:25])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoate

Product 1

HCID 86591009HCID 86591009, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A DMF (100 mL) solution of 2-(4-hydroxyphenoxy)-2-methyl propionic acid ethyl ester (15.2 g, 67.7 mmol) and DABCO (15.2 g, 135.5 mmol) was charged dropwise with N,N-dimethylthiocarbamoyl chloride (16.7 g, 135.5 mmol) in 20 mL DMF over 15 min. The reaction was stirred at room temperature for 18 h and then quenched with water. The reaction was partitioned between water (1L) and ethyl acetate (500 mL) and the organic layer washed with 1N HCl (500 mL). After drying (MgSO4) and concentration, the crude product was obtained as a tan oil. Purification by flash chromatography (15% ethyl acetate/hexane) provided the product (15.8 g, 75%) as a pale yellow oil: 1H NMR (CDCl3) δ1.32 (t, 3H), 1.65 (s, 6H), 3.37 (s, 3H), 3.50 (s, 3H), 4.30 (q, 2H), 6.93 (dd, 4H); MS (m/e) 312.

Workup

  1. customquenched with water
  2. customThe reaction was partitioned between water (1L) and ethyl acetate (500 mL)
  3. washthe organic layer washed with 1N HCl (500 mL)
  4. customAfter drying
  5. concentration(MgSO4) and concentration
  6. customthe crude product was obtained as a tan oil
  7. customPurification by flash chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4e919eb0057c4a3e83470a0cd9a54406
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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