Triphenylphosphine → HCID 136340744, compound

HRID 1603311Notes

Reaction equation

HRID 1603311 reaction equation
CC[O:3]C(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][C@@H:33]([OH:40])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].F[C:42]1[C:47](F)=[C:46](CC[C@H]2CC[C@H](CCCCC)CC2)[CH:45]=[CH:44][C:43]=1[C:62]1[N:67]=[CH:66][C:65]([C:68]([O:70]C[C@H](F)CCCCCC)=O)=[CH:64][N:63]=1>C(Cl)(Cl)Cl.C1COCC1>[OH:3][C:46]1[CH:45]=[CH:44][C:43]([C:62]2[N:67]=[CH:66][C:65]([C:68]([O:40][C@@H:33]([CH3:32])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:70])=[CH:64][N:63]=2)=[CH:42][CH:47]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 80080(R)-2-OctanolHCID 5462977Diethyl azodicarboxylateHCID 178443933HCID 178443933, compound

Product 1

HCID 136340744HCID 136340744, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

--Quantities: hydroxy acid 59 (716 mg, 3.28 mmol), DEAD (572 mg, 3.28 mmol), triphenylphosphine (861 mg, 3.28 mmol), (R)-(-)-octan-2-ol (428 mg, 3.28 mmol), THF (100 ml). The experimental procedure was as described for compound 47. Flash chromatography (10% ethyl acetate-light petroleum) gave the 1-methylheptyl ester 60 (520 mg, 48%) (from EtOH/AcOH), m.p.98.8° C., [α]D22 +44.7° (c 1.7 in CHCl3); νmax /cm-1 (KBr) 3440br, 2920, 1670, 1570, 1430, 1345, 1300, 1165 and 810; δ 0.88 (3H, t), 1.20-1.50 (11H, m), 1.70 (2H, m, CH2CHMe), 5.22 (1H, sext, OCHMe), 6.10 (1H, br s), 6.94 (2H, d, 3'- and 5'-H), 8.42 (2H, d, 2'- and 6'-H) and 9.27 (2H s, 4- and 6-H); m/z 328 (M+),314, 285, 261, 247 216 and 119.

Sources & evidence

ORD record
ord-faa16832764540b89c6cf1972d088bda
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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