Hydrochloric Acid → HCID 53707100, compound
Reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@H:20]([C:21]=2[CH:22]=1)[C@H:19]([O:23]C(=O)C(C)(C)C)[CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]1[O:30]C(=O)C(C)(C)C)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>CCOCC>[CH3:17][C@:16]12[CH2:18][C@@H:19]([OH:23])[C@H:20]3[C@@H:11]([CH2:10][CH2:9][C:8]4[CH:7]=[CH:6][C:5]([OH:4])=[CH:22][C:21]=43)[C@@H:12]1[CH2:13][CH2:14][C@@H:15]2[OH:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the triester (28) (150 mg, 0.30 mmol) in dry ether (3 ml) was treated with lithium aluminium hydride (46 mg, 1.41 mmol) at room temperature. After 5 min ethyl acetate (1 ml) and then dilute hydrochloric acid (1 ml) was added, and the mixture was worked up with ether in the usual manner. Chromatography of the crude product on silica (2 g) eluted with ethyl acetate gave the product (6D) (79 mg, 91%), m.p. 229°-232° C. (from acetone), νmax (KBr disc) 3500 cm-1 (OH), δ (MeOH) (250 MHz) 7.41 (1 H, dd, J 2.5 and 1 Hz, 1-proton), 7.39 (1 H, d, J 8 Hz, 4-proton), 6.86 (1 H, ddd, J 8, 2.5, and 1 Hz, 3-proton), 4.11 (1 H, dt, J 10.5 and 5 Hz, 11-proton), 3.67 (1 H, t, J 8.5 Hz, 17-proton), 3.68 (2 H, t, J 9 Hz, 6-protons), 2.21 (1 H, A part of ABX system, JAX =5 Hz, JAX =12 Hz), 2.20-1.20 (13 H, m), 0.74 (3 H, s, 18-CH3),
Workup
- washChromatography of the crude product on silica (2 g) eluted with ethyl acetate
Sources & evidence
- ORD record
- ord-7f6b97ef53ff406d93dc3a96efd0fd08
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04882439
Reaction notes
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