4-Toluenesulfonyl chloride → HCID 12972966, compound

HRID 324554Notes

Reaction equation

HRID 324554 reaction equation
CC1(C)OC(CS([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=O)=O)CO1.CC1(C)[O:24][CH:23]([CH2:25][OH:26])[CH2:22]O1.CC[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32].[C:35]1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl>[CH2:15]([CH:35]1[CH2:32][CH2:31][N:30]([CH2:22][CH:23]([OH:24])[CH2:25][OH:26])[CH2:33][CH2:34]1)[C:14]1[CH:13]=[CH:12][CH:11]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471TriethylamineHCID 13773449HCID 13773449, compound

Product 1

HCID 12972966HCID 12972966, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

2,2-Dimethyl-4-tosylmethyl-1,3-dioxolane. To a solution of solketal (2.00 mL, 16.0 mmol) in CH2Cl2 (50 mL) was added Et3N (4.50 mL, 32 mmol). A solution of p-toluensulfonyl chloride (4.30 g, 22 mmol) in CH2Cl2 (30 mL) was then added dropwise at 0° C. The resulting solution was stirred at 25° C. for 6 h, then. was diluted with CH2Cl2 (50 mL). This solution was washed with HCl (5%, 100 mL) and brine (100 mL), dried and concentrated in vacuo to afford the crude product. This was purified by flash-chromatography on silica gel using EtOAc/n-hexane as eluant to give the title compound as a colorless oil (2.03 g, 45%): 1H NMR (CDCl3) δ 1.31 (s, 3H), 1.34 (s, 3H), 2.45 (s, 3H), 3.77 (q, J=5.1 and 8.7 Hz, 1H), 3.90-4.10 (m, 3H), 4.28 (p, J=5.7 Hz, 1H), 7.35 (d, J=8.1 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H);

Workup

  1. washThis solution was washed with HCl (5%, 100 mL) and brine (100 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product
  5. customThis was purified by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-56cf3f277d3b47b99a2642aedecb50b6
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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