Dichloromethane → HCID 69921427, compound

HRID 392061Notes

Reaction equation

HRID 392061 reaction equation
N=CCCC[C:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]C=1)O.[NH:22]=[CH:23][CH2:24][CH2:25][CH2:26]CC(CC1C=CC=CC=1)(CC1C=CC=CC=1)O.C1(N(C2C=CC=CC=2)CCCCO)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)[Cl:82]>>[Cl:82][CH2:26][CH2:25][CH2:24][CH2:23][N:22]=[C:12]1[CH:11]=[C:8]([CH:6]=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=[CH:14][CH2:13]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 10879289HCID 10879289, compoundHCID 22662697HCID 22662697, compoundHCID 22662698HCID 22662698, compound

Product 1

HCID 69921427HCID 69921427, compound

Procedure

To prepare compounds 6c, 6d and 6f to a cooled 25 ml round-bottomed flask containing 5c (50 mg, 0.16 mmol), 5d or 5f and Ph3P (51 mg, 0.2 mmol) was added HCA (0.05 ml, 0.3 mmol) in 1 ml CH2Cl2. The reaction mixture was allowed to come to room temperature and stirred overnight. Flash silica gel column chromatography by eluting with hexane to remove the HCA followed by 5% ethyl acetate/hexanes afforded the following compounds:

Workup

  1. customto come to room temperature
  2. washFlash silica gel column chromatography by eluting with hexane
  3. customto remove the HCA
  4. customafforded the following compounds

Sources & evidence

ORD record
ord-34e96af856384c08becb80727db9a761
Source dataset
uspto-grants-2004_10
Patent number
US06800618B2

Reaction notes

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