Dichloromethane → HCID 178472502, compound

HRID 2095645Notes

Reaction equation

HRID 2095645 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(Cl)Cl.C(N(CC)CC)C>>[CH2:11]([O:10][C:8]([C@H:5]1[CH2:4][CH2:3][C@@H:2]([O:1][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:7][CH2:6]1)=[O:9])[CH3:12]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178472486HCID 178472486, compound

Product 1

HCID 178472502HCID 178472502, compound

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl cis-4-hydroxycyclohexanecarboxylate (4.30 g, 25.0 mmol), p-toluenesulfonyl chloride (7.14 g, 37.4 mmol) and DCM (100 mL, 2000 mmol) was added triethylamine (6.96 mL, 49.9 mmol) at rt. The mixture was stirred at 25° C. overnight. The solution was transferred to a separatory funnel, washed with 2 M HCl to remove base, then washed with sat. NaHCO3. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 10-20% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ=1.16 (t, J=7.2 Hz, 3H), 1.52-1.67 (m, 8H), 2.31-2.40 (m, 1H), 2.42 (s, 3H), 4.05 (q, J=7.1 Hz, 2H), 4.66 (br. s., 1H), 7.47 (m, J=7.8 Hz, 2H), 7.80 (m, J=8.3 Hz, 2H).

Workup

  1. customThe solution was transferred to a separatory funnel
  2. washwashed with 2 M HCl
  3. customto remove base
  4. washwashed with sat. NaHCO3
  5. washeluting with 10-20% EtOAc/hexanes
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-96a9a5a7f3ee44c098300dcfa67c61e6
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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