4-Toluenesulfonyl chloride → (+/-)-3-[5-(Benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 13936Notes

Reaction equation

HRID 13936 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[CH:17][C:16]([O:24][CH3:25])=[C:15]2[C:10]=1[CH:11]1[CH2:27][CH2:26][CH:14]2[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>N1C=CC=CC=1>[CH3:38][C:28]1[CH:33]=[CH:32][C:31]([S:34]([O:22][CH2:21][CH:20]([OH:23])[CH2:19][C:18]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]3[C:15](=[C:16]([O:24][CH3:25])[CH:17]=2)[CH:14]2[CH2:13][CH2:12][CH:11]3[CH2:27][CH2:26]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68583372HCID 68583372, compound

Product 1

HCID 86598551(+/-)-3-[5-(Benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treatment of (±)-3-[5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]propane-1,2-diol (15.82 g, 0.043 mol) with p-toluenesulfonyl chloride (9.00 g, 0.047 mol) in anhydrous pyridine (400 mL) generally according to the procedure described for Intermediate 18 gave 20.12 g (90%) of (±)-3-[5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate as a colorless oil. Anal. calcd. for C30H34O6S.0.5H2O: C, 67.77; H, 6.64. Found: C, 67.86; H, 6.55.

Sources & evidence

ORD record
ord-884f18c166d747c29af2df5c299c91f0
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

Loading…