Benzyl Bromide → Butyl 3-(1,3-bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonate

HRID 1259404Notes

Reaction equation

HRID 1259404 reaction equation
[OH:1][CH2:2][CH:3]([CH:6]1[CH2:9][CH:8]([S:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])=[O:11])[CH2:7]1)[CH2:4][OH:5].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+]>C1COCC1>[CH2:18]([O:1][CH2:2][CH:3]([CH:6]1[CH2:7][CH:8]([S:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])=[O:11])[CH2:9]1)[CH2:4][O:5][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 58380541Butyl 3-(1,3-dihydroxypropan-2-yl)cyclobutane-1-sulfonate

Product 1

HCID 58380533Butyl 3-(1,3-bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the same reaction conditions, procedure and work up as described Intermediate I-25a (below), butyl 3-(1,3-dihydroxypropan-2-yl)cyclobutane-1-sulfonate (0.13 g, 0.489 mmol) was reacted with benzyl bromide (0.13 mL, 1.075 mmol), 60% NaH (60 mg, 1.467 mmol) and THF (5 mL) to afford the crude product. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 0.07 g of the product (78% yield).

Workup

  1. customthe same reaction conditions, procedure
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-79bebf9289614ab9ae54bec9b64a6a2a
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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