Benzyl Alcohol → HCID 68530198, compound

HRID 2246553Notes

Reaction equation

HRID 2246553 reaction equation
[CH3:1][Si:2]([CH3:42])([CH2:31][CH2:32][CH2:33][O:34][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])[CH2:3][CH2:4][C:5]1[C:17]2[CH2:16][N:15]3[C:10](=[CH:11][C:12]4[C:22]([CH2:24][CH3:25])([OH:23])[C:21](=[O:26])[O:20][CH2:19][C:13]=4[C:14]3=[O:18])[C:9]=2[N:8]=[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=12.N1C=CC=CC=1.[C:49](Cl)(Cl)=[O:50].[CH2:53]([OH:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:42][Si:2]([CH3:1])([CH2:31][CH2:32][CH2:33][O:34][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])[CH2:3][CH2:4][C:5]1[C:17]2[CH2:16][N:15]3[C:10](=[CH:11][C:12]4[C:22]([O:23][C:49](=[O:50])[O:60][CH2:53][C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)([CH2:24][CH3:25])[C:21](=[O:26])[O:20][CH2:19][C:13]=4[C:14]3=[O:18])[C:9]=2[N:8]=[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=12

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 6371PhosgeneHCID 68529807HCID 68529807, compound

Product 1

HCID 68530198HCID 68530198, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of Compound 51 (1.21 g, 2 mmol), 4-dimethylaminopyridine (244 mg, 2 mmol) and pyridine (1.62 mL, 20 mmol) in dichloromethane (20 mL) at −10° C. was added phosgene (20% in toluene, 2.10 mL, 4 mmol) dropwise. The resulting mixture was stirred for 15 minutes at −10° C. Benzyl alcohol (0.83 mL, 8 mmol) was added and the resulting mixture was stirred at 21° C. for 2 hours. The reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to afford yellow oil, which was chromatographed to give the desired product (Yield: 47%).

Workup

  1. stirringthe resulting mixture was stirred at 21° C. for 2 hours
  2. customThe reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer
  3. extractionwas extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford yellow oil, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-7c494ff28d2c49eb9381a429b1b588b7
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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