Tetrahydrofuran → HCID 462612, compound

HRID 743092Notes

Reaction equation

HRID 743092 reaction equation
C(N(CC)CC)C.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[OH:14][CH2:15][C:16]1[S:17][S:18][C:19]([CH2:22][OH:23])=[CH:20][CH:21]=1.S1C=CC=CS1.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>CCOCC>[CH:8]1([C:11]([O:14][CH2:15][C:16]2[S:17][S:18][C:19]([CH2:22][O:23][C:34]([CH:33]3[CH2:31][CH2:32]3)=[O:30])=[CH:20][CH:21]=2)=[O:12])[CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 462608155698-98-9HCID 120445651,2-Dithiin

Product 1

HCID 462612HCID 462612, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of triethylamine (0.30 mL) in tetrahydrofuran (2.0 mL) at 0° C. was added dropwise cyclopropanecarbonyl chloride (0.10 mL) followed by the addition of 3,6-bis(hydroxymethyl)-1,2-dithiin, Dithiin A (20 mg, 0.113 mmol) in tetrahydrofuran (1.0 mL). After stirring in the dark at room temperature overnight the mixture was diluted with ether (20 mL) and partitioned between 1.0M H3PO4 (80 mL) and diethyl ether (30 mL). The diethyl ether layer was washed with saturated NaHCO3 (100 mL), dried (Na2SO4), and evaporated to give a red oil (31.5 mg): 1H NMR (CDCl3) δ6.38 (s, 2H), 4.71 (s, 4H), 1.67 (m, 2H), 1.04 (m, 4H), 0.92 (m, 4H).

Workup

  1. custompartitioned between 1.0M H3PO4 (80 mL) and diethyl ether (30 mL)
  2. washThe diethyl ether layer was washed with saturated NaHCO3 (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-29a21e21d3714fc7849276b899627a55
Source dataset
uspto-grants-1996_09
Patent number
US05556875

Reaction notes

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