Benzyl Bromide → HCID 86760327, compound

HRID 857955Notes

Reaction equation

HRID 857955 reaction equation
[H-].[Na+].[CH3:3][C:4]([Si:7]([CH3:58])([CH3:57])[O:8][C@H:9]([C@@H:27]([CH3:56])[CH2:28]/[C:29](/[CH3:55])=[CH:30]\[C@H:31]([CH3:54])[C@@H:32]([O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[C@@H:33]([CH3:45])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[C@H:10]([CH3:26])[C@@H:11]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C@@H:12]([CH3:15])[CH2:13][OH:14])([CH3:6])[CH3:5].[CH2:59](Br)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>CN(C=O)C.[I-].[K+]>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][O:16][C@@H:11]([C@@H:12]([CH3:15])[CH2:13][O:14][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@H:10]([CH:9]([O:8][Si:7]([CH3:57])([CH3:58])[C:4]([CH3:6])([CH3:5])[CH3:3])[CH:27]([CH3:56])[CH2:28][C:29]([CH3:55])=[CH:30][CH:31]([CH3:54])[CH:32]([C@@H:33]([CH3:45])[CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[O:46][Si:47]([CH3:48])([CH3:49])[C:50]([CH3:53])([CH3:52])[CH3:51])[CH3:26])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12136221HCID 12136221, compound

Product 1

HCID 86760327HCID 86760327, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

NaH (12 mg, 0.49 mmol, 2 eq) is added to a solution of (2S,3S,4R,5R,6S,8Z,10S,11R,12S)-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyl-8-tridecen-1-ol (200 mg, 0.245 mmol, 1 eq) in DMF (3 mL) at −78° C. The reaction is slowly warm to 23° C. and is stirred for 1 h. Benzyl bromide (84 mg, 0.49 mmol, 2 eq) and potassium iodide (cat. 1 mg) are added and stirred for 18 h. The solvent is removed. The crude product is chromatographed (from hexane to 10% EtOAc in hexane) to give 204 mg (80%) of the desired compound as a colorless oil.

Workup

  1. stirringstirred for 18 h
  2. customThe solvent is removed
  3. customThe crude product is chromatographed (from hexane to 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-6c878f683f254b7ab890b2aff8f675dd
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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