Triphenylphosphine → (+/-)-(5-Methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate

HRID 13938Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:30])[CH2:14][C:15]2[C:16](O)=[C:17]3[C:22](=[C:23]([O:25][CH3:26])[CH:24]=2)[CH:21]2[CH2:27][CH2:28][CH:18]3[CH2:19][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:30][C:16]3[C:17]4[CH:18]5[CH2:19][CH2:20][CH:21]([C:22]=4[C:23]([O:25][CH3:26])=[CH:24][C:15]=3[CH2:14]2)[CH2:27][CH2:28]5)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 86598552(+/-)-2-Hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate

Product 1

HCID 86598553(+/-)-(5-Methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonateYield 75.1%

Procedure

Treatment of (±)-2-hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate (15.14 g, 35.0 mmol) with triphenylphosphine (10.10 g, 38.5 mmol) followed by diethylazodicarboxylate (6.71 g, 38.5 mmol) generally according to the procedure described for Intermediate 5 afforded 10.9 g (75%) of (±)-(5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate as a white solid. mp 136-141° C.; Anal. calcd. for C23H26O5S: C, 66.64; H, 6.32. Found: C, 66.53; H, 6.51.

Sources & evidence

ORD record: ord-b8e797c240de4e019d869b0001db58ea
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Reaction notes

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