Dichloromethane → HCID 68006372, compound

HRID 1026530Notes

Reaction equation

HRID 1026530 reaction equation
C(N=C=NC(C)C)(C)C.[C:10](O)([CH3:13])([CH3:12])[CH3:11].ClCCl.[OH:18][C:19]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20]1>[Cu]Cl.C(O)(=O)C>[OH:18][C:19]1([C:22]([O:24][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:23])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 12734DiisopropylcarbodiimideHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Product 1

HCID 68006372HCID 68006372, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent

Procedure

At room temperature under shielded light, to N,N′-diisopropylcarbodiimide (99.75 g) was added copper(I) chloride (1.57 g), and then tert-butanol (83 ml) was added dropwise over 20 minutes, followed by stirring for 4 days. The supernatant (48 ml) was added dropwise to a dichloromethane suspension (120 ml) of 1-hydroxycyclopropanecarboxylic acid (17.12 g) using an ice bath over 15 minutes. The temperature was brought back to room temperature, followed by stirring for 40 hours, and then acetic acid (11.5 ml) was added and stirred for 1 hour. The reaction suspension was filtered, and ice water and sodium hydrogen carbonate were added to the filtrate for neutralization. After the precipitate was filtered off, the organic layer separated from the filtrate was washed with saturated sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After pentane was added to the residue, insolubles were filtered off, and the filtrate was concentrated under reduced pressure to afford tert-butyl 1-hydroxycyclopropanecarboxylate (11.65 g).

Workup

  1. customover 15 minutes
  2. customwas brought back to room temperature
  3. stirringby stirring for 40 hours
  4. stirringstirred for 1 hour
  5. filtrationThe reaction suspension was filtered
  6. additionice water and sodium hydrogen carbonate were added to the filtrate for neutralization
  7. filtrationAfter the precipitate was filtered off
  8. customthe organic layer separated from the filtrate
  9. washwas washed with saturated sodium hydrogen carbonate
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionAfter pentane was added to the residue, insolubles
  13. filtrationwere filtered off
  14. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0cbfc76e7a54dbcbe1e9dffdb4695de
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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