Triphenylphosphine → HCID 86599065, compound

HRID 2115915Notes

Reaction equation

HRID 2115915 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:29])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]=2O)(=[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[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:16]=3[O:29]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86599064HCID 86599064, compound

Product 1

HCID 86599065HCID 86599065, compoundYield 94%

Procedure

Treatment of (±)-3-(3-benzyl-2-hydroxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonate (7.29 g, 0.018 mol) with triphenylphosphine (5.10 g, 0.019 mol) and diethylazodicarboxylate (3.39 g, 0.019 mol) generally according to the procedure described for Intermediate 5 afforded 6.57 g (94%) of (±)-(7-benzyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a colorless oil. Anal. calcd. for C23H22O4S: C, 70.03; H, 5.62. Found: C, 68.97; H, 5.42.

Sources & evidence

ORD record
ord-fe582aabf78148079e98a99f0ecc819a
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…