Acetyl chloride → HCID 68015075, compound

HRID 1913027Notes

Reaction equation

HRID 1913027 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]4[O:48][CH2:47][CH2:46][C:45]=4[CH:49]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C@@H:10]1CC(C(C)(C)C)(C)O[SiH3])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:59](Cl)(=[O:61])C>CO>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:42]=[CH:43][C:44]4[O:48][CH2:47][CH2:46][C:45]=4[CH:49]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C@@H:10]1[CH2:59][OH:61])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 137328607HCID 137328607, compound

Product 1

HCID 68015075HCID 68015075, compoundYield 586.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-methoxy-tetrahydropyran-2-yl]tert-butyl-dimethyl-methoxy]silane 5g (11.86 g, 14.4 mmol) was dissolved in 100 mL methanol, followed by addition of acetyl chloride (152 μL, 2.17 mmol). The reaction mixture was stirred for 1 hour and concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 5h (9.0 g, yellow liquid), yield: 88.1%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography with elution system D

Sources & evidence

ORD record
ord-4fa9900e8bbb4e29a1f4ffafa1a898dc
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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