Benzyl Bromide → HCID 10653622, compound

HRID 1401059Notes

Reaction equation

HRID 1401059 reaction equation
[C:1]([O:20][CH2:21][C@H:22]([C@H:24]([C@@H:26]([C@@H:28]([CH2:30][O:31][C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[OH:29])[OH:27])[OH:25])[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:53](Br)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[C:1]([O:20][CH2:21][C@H:22]([C@H:24]([C@@H:26]([C@@H:28]([CH2:30][O:31][C:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[O:29][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:27][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:25][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[O:23][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10556358HCID 10556358, compound

Product 1

HCID 10653622HCID 10653622, compoundYield 219%

Procedure

10.64 g (16 mmol) of 1,6-di-O-trityl-D-mannitol and 3.07 g of NaH (60% oil dispersion) were added into a 250 mL round-bottom flask. The flask was purged with N2 and cooled in a dry ice/isopropanol bath, and then 133 mL of anhydrous DMF was added. After stirring for 5 min, 8.55 mL (72 mmol) of benzyl bromide was added slowly to the reaction mixture. The dry ice/iPrOH bath was removed and the reaction mixture stirred at RT for 3.5 hr and then concentrated under reduced pressure. 400 mL of EtOAc and 300 mL of deionized water were added to the residue. After separation, the water layer was back extracted twice with EtOAc. The combined EtOAc layers were washed three times with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain 18 g of desired product (yield: 109%). The product was used directly for the next reaction without further purification. Mass spec analysis (MALDI-TOF): exact mass: 1026.49, obtained: 1050.85 [M+Na]+.

Workup

  1. customThe flask was purged with N2
  2. temperaturecooled in a dry ice/isopropanol bath
  3. addition133 mL of anhydrous DMF was added
  4. customThe dry ice/iPrOH bath was removed
  5. stirringthe reaction mixture stirred at RT for 3.5 hr
  6. concentrationconcentrated under reduced pressure
  7. addition400 mL of EtOAc and 300 mL of deionized water were added to the residue
  8. customAfter separation
  9. extractionthe water layer was back extracted twice with EtOAc
  10. washThe combined EtOAc layers were washed three times with brine
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e669f576b1614c7399a0fc3485666ec7
Source dataset
uspto-grants-2014_12
Patent number
US08907079B2

Reaction notes

Loading…