Lithium tri-s-butylborohydride → HCID 66692593, compound

HRID 2215276Notes

Reaction equation

HRID 2215276 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].C[C:16]1[CH:25]=[C:24](C)[CH:23]=[C:22]2[C:17]=1[CH2:18][C:19](=[O:57])[CH:20]([C:27]1[CH:32]=[C:31](OCC3C=CC=CC=3)[C:30](OCC3C=CC=CC=3)=[C:29](OCC3C=CC=CC=3)[CH:28]=1)[O:21]2.O1C2C(=CC=CC=2)CC(O)C1C1C=CC=CC=1>>[O:21]1[C:22]2[C:17](=[CH:16][CH:25]=[CH:24][CH:23]=2)[CH2:18][C@H:19]([OH:57])[C@@H:20]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 3611392Lithium tri-s-butylborohydrideHCID 37072431481-83-0HCID 21920903HCID 21920903, compound

Product 1

HCID 66692593HCID 66692593, compound

Procedure

Preparation of (2,3-Cis)-5,7-dimethyl-2-(3,4,5-tribenzyloxyphenyl)chroman-3-ol (30): The cis 3-flavanol 30 was synthesized by the stereoselective L-selectride reduction of the 3-flavanone 29 in the same manner as given for 3-flavanol 23 (Scheme 3). The final product was obtained as a colorless oil (62% yield), after flash chromatography on silica gel using 20% of ethyl acetate in hexanes. 1H NMR (300 MHz, CDCl3): δ 1.73 (s, 1H, OH), 2.20 (s, 3H, CH3), 2.27 (s, 3H, CH3), 2.83 (d, J=17.1 Hz, 1H, 4-H), 2.95 (dd, J=4.2, 17.1 Hz, 1H, 4-H), 4.23–4.28 (m, 1H, 3-H), 4.87 (s, 1H, 2-H), 5.06 (s, 2H, OCH2Ph), 5.13 (s, 4H, OCH2Ph), 6.66 (s, 1H, 8-H), 6.68 (s, 1H, 6-H), 6.81 (s, 2H, 2′, 6′-H), 7.25–7.43 (m, 15H, Ar—H). MS (ESI, positive ion) 595 (M+Na), 1167 (2M+Na).

Sources & evidence

ORD record
ord-e535e3fa6cc2406b99875c1abe3569d6
Source dataset
uspto-grants-2006_09
Patent number
US07109236B2

Reaction notes

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