Water → 2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thiazole

HRID 1016040Notes

Reaction equation

HRID 1016040 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1(O)[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.S(Cl)(Cl)=O.O.CCOC(C)=O>N1C=CC=CC=1>[O:10]1[C:9]2([CH2:14][CH2:15][C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH2:8]2)[O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 595561422-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thiazoleYield 36.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (0.8 g, 3.32 mmol) in pyridine (10 mL) at 0° C. was added thionyl chloride (2.5 mL, 34.3 mmol) under N2. After being stirred for 2 h at 0° C. under N2, water and EtOAc were added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed using 10% EtOAc/hexane to give 0.27 g of the title compound in 36% yield. MS (EI) calcd: (M+1)+=224.1; found: 224.2.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×)
  2. washThe combined organic layers were washed with saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customflash chromatographed

Sources & evidence

ORD record
ord-ce3ffd9f66d44bad86df419dbe549a7a
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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