Phosphorus oxychloride → 3-(1,3-Bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonyl chloride

HRID 1259406Notes

Reaction equation

HRID 1259406 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH:20]1[CH2:23][CH:22]([S:24]([O-:27])(=O)=[O:25])[CH2:21]1)[CH2:11][O:12][CH2:13][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.[K+].O=P(Cl)(Cl)[Cl:31].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]([CH:20]1[CH2:23][CH:22]([S:24]([Cl:31])(=[O:27])=[O:25])[CH2:21]1)[CH2:11][O:12][CH2:13][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

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 86656334Potassium 3-(1,3-bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonate

Product 1

HCID 583805443-(1,3-Bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonyl chlorideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same reaction conditions, procedure and work up as described for the preparation of Intermediate I-25c (below), potassium 3-(1,3-bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonate (0.5 g, 1.168 mmol) was reacted with POCl3 (0.22 mL, 2.336 mmol), diisopropyl ethyl amine (0.4 mL, 2.336 mmol) and DCM (20 mL) to afford the crude product. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 0.32 g of the product (68% 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-eb0c9f97b7734cfda67df2ba6c7997e8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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