1-Dodecanethiol → HCID 131733391, compound

HRID 2274371Notes

Reaction equation

HRID 2274371 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16]2[CH:21]=[C:20]([CH:22]=[CH2:23])[CH:19]=[CH:18][C:17]=2[O:24]COC)[C:13]([CH2:28][CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(S)CCCCCCCCCCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Zn+2].[Br-].[Br-]>[Si:1]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16]2[CH:21]=[C:20]([CH:22]=[CH2:23])[CH:19]=[CH:18][C:17]=2[OH:24])[C:13]([CH2:28][CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81951-DodecanethiolHCID 516892Sodium BicarbonateHCID 131733392HCID 131733392, compound

Product 1

HCID 131733391HCID 131733391, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20 (1.3 g, 2.4 mmol) in CH2Cl2 (25 mL) at 0° C. was added ZnBr2 (0.59 g, 2.6 mmol) followed by 1-dodecane thiol (1.1 mL, 4.8 mmol). Then the reaction mixture was stirred for 10 minutes, diluted with CH2Cl2 (60 mL), then NaHCO3 (sat) solution was added dropwise and the mixture was filtered through a pad of celite. The aqueous layer was separated and further extracted with CH2Cl2. The combined organic solution was dried with Na2SO4, volatiles were removed in vacuo to provide crude product and column chromatography on silica gel using [hexane/EtOAc (90:10)] provided 21 (1.12 g, 2.22 mmol, 93%) as a clear liquid.

Workup

  1. filtrationthe mixture was filtered through a pad of celite
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with CH2Cl2
  4. dry with materialThe combined organic solution was dried with Na2SO4, volatiles
  5. customwere removed in vacuo
  6. customto provide crude product and column chromatography on silica gel using [hexane/EtOAc (90:10)]

Sources & evidence

ORD record
ord-fc1f8ca8448b4f93b00719d6fed47c51
Source dataset
uspto-grants-2015_09
Patent number
US09126965B1

Reaction notes

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