Dichloromethane → HCID 70153917, compound

HRID 1936190Notes

Reaction equation

HRID 1936190 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].Cl[CH2:7][CH2:8][C@H:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[OH:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)[Cl:35]>>[CH2:1]([O:3][CH:4]([O:10][C@@H:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([Cl:35])[CH2:12]1)[CH2:8][CH3:7])[CH3:5])[CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8023Ethyl vinyl ether2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 11788595HCID 11788595, compound

Product 1

HCID 70153917HCID 70153917, compoundYield 97%

Procedure

Ethyl vinyl ether (EVE) (10 mL) was added to a stirred, ice-cooled solution of (R)-3-chloro-1-cyclohexyl-1-propanol (4.89 g, 27.7 mmol) and pyridinium p-toluenesulfonate (PPTS) (0.04 g) in 40 mL of dry CH2Cl2. After 10 minutes, 0.20 g of PPTS and 8 mL of EVE were added, and the solution was allowed to warm to RT. After 1 hour, the solution was filtered through a pad of silica, eluting with diethyl ether. Concentration afforded 6.69 g (97%) of (R)-1-(3-chloro-1-cyclohexyl)propyl (1-ethoxyethyl) ether. NMR (CDCl3) δ0.9-2.0 (m, 13H), 1.21 (t, J=7.0, 3H), 1.30 and 1.32 (2 overlapping d, J=5.3, 3H), 3.4-3.8 (m, 5H), 4.7 (2 overlapping q, J=5.3, 1H).

Workup

  1. waitAfter 1 hour
  2. filtrationthe solution was filtered through a pad of silica
  3. washeluting with diethyl ether
  4. concentrationConcentration

Sources & evidence

ORD record
ord-9a0f1396f09d41ba9ab9e349ebdcf561
Source dataset
uspto-grants-2002_05
Patent number
US06388128B1

Reaction notes

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