Dabco → HCID 86591009, compound

HRID 898478Notes

Reaction equation

HRID 898478 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 rt for 18 h and then quenched with water. The reaction was partitioned between water (1 L) and EtOAc (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% EtOAc/hexane) provided the product (15.8 g, 75%) as a pale yellow oil: 1H NMR (CDCl3) δ 1.32 (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 (1 L) and EtOAc (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% EtOAc/hexane)

Sources & evidence

ORD record
ord-4fb684a6a7c74f608df29535f3009aa1
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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