Ammonium Chloride → HCID 69552008, compound

HRID 984533Notes

Reaction equation

HRID 984533 reaction equation
[CH3:1][C:2]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:42])[CH:40]=[O:41])=[CH:3][CH2:4][CH:5]([O:15][C:16](=[O:35])[CH2:17][CH:18]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:19]([CH3:26])([CH3:25])[C:20](=[O:24])[CH:21](Br)[CH3:22])[C:6]([CH3:14])=[CH:7][C:8]1[N:9]=[C:10]([CH3:13])[S:11][CH:12]=1.[Li+].[I-].[NH4+].[Cl-]>O1CCCC1>[C:31]([Si:28]([CH3:30])([CH3:29])[O:27][CH:18]1[C:19]([CH3:26])([CH3:25])[C:20](=[O:24])[CH:21]([CH3:22])[CH:40]([OH:41])[CH:39]([CH3:42])[CH2:38][CH2:37][CH2:36][C:2]([CH3:1])=[CH:3][CH2:4][CH:5]([C:6]([CH3:14])=[CH:7][C:8]2[N:9]=[C:10]([CH3:13])[S:11][CH:12]=2)[O:15][C:16](=[O:35])[CH2:17]1)([CH3:33])([CH3:32])[CH3:34]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66321Lithium iodideHCID 72615810HCID 72615810, compound

Product 1

HCID 69552008HCID 69552008, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 80 mg (0.117 mmol) 6-bromo-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-5-oxo-heptanoic acid 4,8-dimethyl-1-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-9-oxo-non-3-enyl ester in 5.0 ml absolute tetrahydrofurane was added to a suspension of 35 mg (0.285 mmol) CrCl2 and 30 mg (0.224 mmol) LiI in 25 ml dry tetrahydrofurane within 80 min using a syringe pump. After addition was completed, the resulting suspension was stirred for another 2 hrs at ambient temperature. Then, 20 ml semiconcentrated NH4Cl solution was added, and the organic phase was extracted with diethylether (5×15 ml). The organic phases were combined, and washed twice with 15 ml demin. water as well as twice with 15 ml saturated NaCl solution, dried over Na2SO4, filtered, and concentrated in vacuo. This gave 67 mg of a yellow oil.

Workup

  1. additionAfter addition
  2. extractionthe organic phase was extracted with diethylether (5×15 ml)
  3. washwashed twice with 15 ml demin
  4. dry with materialwater as well as twice with 15 ml saturated NaCl solution, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e73130d0aa24418959c605663bbce49
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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