Hexane → (3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol

HRID 493071Notes

Reaction equation

HRID 493071 reaction equation
CCCCCC.[CH3:7][CH:8]([CH2:11][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[CH2:9]O.[CH2:18]([O:25]COC[C@@H](C)COS(C1C=CC(C)=CC=1)(=O)=O)[C:19]1C=CC=C[CH:20]=1>O>[CH3:7][C@@H:8]([CH2:11][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])/[CH:9]=[CH:20]\[CH2:19][CH2:18][OH:25]

Participants

5

Reactant 3

HCID 8058HexaneHCID 20554058HCID 20554058, compoundHCID 57680470(R)-Toluene-4-sulfonic acid 3-benzyloxymethoxy-2-methyl-propyl ester

Product 1

HCID 57680494(3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

UV (hexane) λmax 234.0 (ε27 800), 241.0 (ε30 200), 248.5 (sh, ε19 900) nm; 1H NMR (400 Hz, CDCl3) δ0.86 (3H, d, J=6.5 Hz, CH—CH3), 1.21 [6H, s, C(CH3)2], 2.08 (2H, q, J=6.9 Hz, 4′-H2), 2.26 (1H, dd, J=13.1, 7.1 Hz), 2.39(1H, dd, J=13.4, 7.2 Hz), 2.56 (1H, dd, J=13.5, 4.2 Hz), 2.70 (1H, dd, J=13.3, 4.3 Hz), 4.48 (2H, m, 1- and 3-H), 5.10 (2H, s, C═CH2); 5.70 (1H, dt, J=15.0, 6.9 Hz, 3′-H 6.03 (1H, d, J=10.8 Hz, 1′-H), 6.29 (1H, dd, J=15.0, 10.8 Hz, 2′-H); MS (El) m/z (relative intensity) no M+, 318 (M+−H2O, 19), 300 (8), 285 (4), 59 (100); HRMS (ESI) exact mass calculated for C21H34O2 (M+−H2O) 318.2559, measured 318.2570.

Sources & evidence

ORD record
ord-0a4ae9895a91429c89fa7b4d954b2150
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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